TY  - CONF
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2023
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6722
AB  - Proučavano jedinjenje (slika 1) sintetisano je polazeći od cikloheksanona Bučerer- Bergsovom reakcijom i naknadnim acilovanjem dobijenog spirohidantoina. Izgradnja kristalne strukture ovog jedinjenja proučavana je sa aspekta doprinosa jednostavnih dimernih motiva koji se uspostavljaju preko različitih intermolekulskih interakcija.
Intermolekulske interakcije dodatno su proučavane pomoću Hiršfeldovih površina i 2D grafičkih prikaza otisaka interakcija. Kristalna struktura, naime, zadržava motiv koji se često sreće kod derivata hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O vodoničnih veza. Ovaj motiv formira dva tipa dvostrukih lanaca, koji dalje grade sloj (slika 2). Osim toga, slabe C–H⋯O interakcije zajedno sa disperzionim interakcijama (π-π i hidrofobne interakcije) identifikovane su u ovoj kristalnoj strukturi. Kristalografski	podaci:		C19H24N2O3, Mr = 328,4, trikliničan sistem, prostorna grupa P–1, a = 6,2810(2),	b = 12,0586(4),	c = 12,1852(5) Å,
α = 77,624(3),	β = 81,039(3),	γ = 79,111(3) °,
 
 
V = 878.81(6) Å3, Z = 2, F(000) = 352, ρx = 1,380 g cm–3,
µ(MoKα) = 0,084 mm–1. Utačnjavanje sa F2 (220 parametara) dalo je R1 = 0,0520, wR2 = 0,1199, S = 1,033 za sve podatke i R1 = 0,0443 za 3232 uočenih refleksija sa I ≥ 2σ(I).
AB  - The title compound (Figure 1) was prepared from cyclohexanone in the Bucherer-Bergs reaction, followed by acylation of the obtained spirohydantoin. Formation of the crystal structure of this compound was analysed in terms of a number of simple dimeric motifs which are associated with different intermolecular interactions. The crystal structure retains the motif commonly found in hydantoin derivatives, where two molecules related by inversion are linked by a pair of N–H O hydrogen bonds. This motif is involved in two types of double chains, which
further form a layer (Figure 2). Intermolecular interactions were also investigated using Hirshfeld surface analysis and 2D fingerprint analysis. Weak C–H⋯O interactions together with the
dispersion interactions (π-π and hydrophobic) as the source of attraction are identified in this crystal structure.
Crystal data: C19H24N2O3, Mr = 328.4, triclinic system, space group P–1, a = 6.2810(2), b = 12.0586(4), c = 12.1852(5) Å, a = 77.624(3), β = 81.039(3), γ = 79.111(3) °, V = 878.81(6) Å3, Z = 2, F(000) = 352,
ρx = 1.380 g cm–3, µ(MoKa) =
= 0.084 mm–1. The refinement on F2 (220 parameters) yielded R1 = 0.0520, wR2 = 0.1199,
S = 1.033 for all data, and R1 = 0.0443 for 3232 observed reflections with I ≥ 2σ(I).
PB  - Beograd : Srpsko kristalografsko društvo
C3  - Izvodi radova / XXVIII konferencija Srpskog kristalografskog društva, Čačak, 14–15. jun 2023
T1  - ULOGA STRUKTURNIH MOTIVA U IZGRADNJI SUPRAMOLEKULSKE ARHITEKTURE 3-(4-TERC-BUTILBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA
T1  - ROLE OF STRUCTURAL MOTIFS IN FORMATION OF THE SUPRAMOLECULAR ARCHITECTURE OF 3-(4-TERT-BUTYLBENZOYL)-1,3-DIAZASPIRO[4.5]DECANE-2,4-DIONE
EP  - 57
SP  - 56
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6722
ER  - 

@conference{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2023",
abstract = "Proučavano jedinjenje (slika 1) sintetisano je polazeći od cikloheksanona Bučerer- Bergsovom reakcijom i naknadnim acilovanjem dobijenog spirohidantoina. Izgradnja kristalne strukture ovog jedinjenja proučavana je sa aspekta doprinosa jednostavnih dimernih motiva koji se uspostavljaju preko različitih intermolekulskih interakcija.
Intermolekulske interakcije dodatno su proučavane pomoću Hiršfeldovih površina i 2D grafičkih prikaza otisaka interakcija. Kristalna struktura, naime, zadržava motiv koji se često sreće kod derivata hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O vodoničnih veza. Ovaj motiv formira dva tipa dvostrukih lanaca, koji dalje grade sloj (slika 2). Osim toga, slabe C–H⋯O interakcije zajedno sa disperzionim interakcijama (π-π i hidrofobne interakcije) identifikovane su u ovoj kristalnoj strukturi. Kristalografski	podaci:		C19H24N2O3, Mr = 328,4, trikliničan sistem, prostorna grupa P–1, a = 6,2810(2),	b = 12,0586(4),	c = 12,1852(5) Å,
α = 77,624(3),	β = 81,039(3),	γ = 79,111(3) °,
 
 
V = 878.81(6) Å3, Z = 2, F(000) = 352, ρx = 1,380 g cm–3,
µ(MoKα) = 0,084 mm–1. Utačnjavanje sa F2 (220 parametara) dalo je R1 = 0,0520, wR2 = 0,1199, S = 1,033 za sve podatke i R1 = 0,0443 za 3232 uočenih refleksija sa I ≥ 2σ(I)., The title compound (Figure 1) was prepared from cyclohexanone in the Bucherer-Bergs reaction, followed by acylation of the obtained spirohydantoin. Formation of the crystal structure of this compound was analysed in terms of a number of simple dimeric motifs which are associated with different intermolecular interactions. The crystal structure retains the motif commonly found in hydantoin derivatives, where two molecules related by inversion are linked by a pair of N–H O hydrogen bonds. This motif is involved in two types of double chains, which
further form a layer (Figure 2). Intermolecular interactions were also investigated using Hirshfeld surface analysis and 2D fingerprint analysis. Weak C–H⋯O interactions together with the
dispersion interactions (π-π and hydrophobic) as the source of attraction are identified in this crystal structure.
Crystal data: C19H24N2O3, Mr = 328.4, triclinic system, space group P–1, a = 6.2810(2), b = 12.0586(4), c = 12.1852(5) Å, a = 77.624(3), β = 81.039(3), γ = 79.111(3) °, V = 878.81(6) Å3, Z = 2, F(000) = 352,
ρx = 1.380 g cm–3, µ(MoKa) =
= 0.084 mm–1. The refinement on F2 (220 parameters) yielded R1 = 0.0520, wR2 = 0.1199,
S = 1.033 for all data, and R1 = 0.0443 for 3232 observed reflections with I ≥ 2σ(I).",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVIII konferencija Srpskog kristalografskog društva, Čačak, 14–15. jun 2023",
title = "ULOGA STRUKTURNIH MOTIVA U IZGRADNJI SUPRAMOLEKULSKE ARHITEKTURE 3-(4-TERC-BUTILBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA, ROLE OF STRUCTURAL MOTIFS IN FORMATION OF THE SUPRAMOLECULAR ARCHITECTURE OF 3-(4-TERT-BUTYLBENZOYL)-1,3-DIAZASPIRO[4.5]DECANE-2,4-DIONE",
pages = "57-56",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6722"
}

Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Đorđević, I.,& Trišović, N.. (2023). ULOGA STRUKTURNIH MOTIVA U IZGRADNJI SUPRAMOLEKULSKE ARHITEKTURE 3-(4-TERC-BUTILBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA. in Izvodi radova / XXVIII konferencija Srpskog kristalografskog društva, Čačak, 14–15. jun 2023
Beograd : Srpsko kristalografsko društvo., 56-57.
https://hdl.handle.net/21.15107/rcub_technorep_6722

Lazić A, Radovanović L, Rogan J, Janjić G, Đorđević I, Trišović N. ULOGA STRUKTURNIH MOTIVA U IZGRADNJI SUPRAMOLEKULSKE ARHITEKTURE 3-(4-TERC-BUTILBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA. in Izvodi radova / XXVIII konferencija Srpskog kristalografskog društva, Čačak, 14–15. jun 2023. 2023;:56-57.
https://hdl.handle.net/21.15107/rcub_technorep_6722 .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "ULOGA STRUKTURNIH MOTIVA U IZGRADNJI SUPRAMOLEKULSKE ARHITEKTURE 3-(4-TERC-BUTILBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA" in Izvodi radova / XXVIII konferencija Srpskog kristalografskog društva, Čačak, 14–15. jun 2023 (2023):56-57,
https://hdl.handle.net/21.15107/rcub_technorep_6722 .

TY  - CONF
AU  - Lazić, Anita M.
AU  - Đorđević, Ivana S.
AU  - Radovanović, Lidija D.
AU  - Popović, Dragan M.
AU  - Rogan, Jelena R.
AU  - Trišović, Nemanja P.
AU  - Janjić, Goran V.
PY  - 2023
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6765
AB  - The hierarchical development of the crystal structure of racemic 3-(4-methoxybenzyl)-6,7-
benzo-1,3-diazaspiro[4.5]decane-2,4-dione was analyzed through cooperativity of various homo
and heterochiral dimeric motifs associated with the presence of different intermolecular
interactions, namely strong N–H···O and weaker C–H···O, C–H···π and PILOs.1 Although a
bigger number of the contacts in the environment of the tetralin unit results from its larger
contact surface, the 4-methoxybenzyl unit provides a greater contribution to the overall
stabilization. In addition, the investigated compound is identified as a potential inhibitor of
kinase enzymes and AG protein-coupled receptors, with a slightly higher affinity for the later
enzyme. An analysis of the nature of the amino acid residues around the tetralin and 4-methoxy
benzyl units revealed that interactions with nonpolar groups are the most prevalent and even
more numerous than interactions with other amino acid residues (polar, positive and negative).
PB  - COST Action CA21101 "COSY"
C3  - Book of Abstracts / COST Training School-Cost action CA21101 COSY "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications", Belgrade, 19th – 22nd September, 2023
T1  - Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone
SP  - 47
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6765
ER  - 

@conference{
author = "Lazić, Anita M. and Đorđević, Ivana S. and Radovanović, Lidija D. and Popović, Dragan M. and Rogan, Jelena R. and Trišović, Nemanja P. and Janjić, Goran V.",
year = "2023",
abstract = "The hierarchical development of the crystal structure of racemic 3-(4-methoxybenzyl)-6,7-
benzo-1,3-diazaspiro[4.5]decane-2,4-dione was analyzed through cooperativity of various homo
and heterochiral dimeric motifs associated with the presence of different intermolecular
interactions, namely strong N–H···O and weaker C–H···O, C–H···π and PILOs.1 Although a
bigger number of the contacts in the environment of the tetralin unit results from its larger
contact surface, the 4-methoxybenzyl unit provides a greater contribution to the overall
stabilization. In addition, the investigated compound is identified as a potential inhibitor of
kinase enzymes and AG protein-coupled receptors, with a slightly higher affinity for the later
enzyme. An analysis of the nature of the amino acid residues around the tetralin and 4-methoxy
benzyl units revealed that interactions with nonpolar groups are the most prevalent and even
more numerous than interactions with other amino acid residues (polar, positive and negative).",
publisher = "COST Action CA21101 "COSY"",
journal = "Book of Abstracts / COST Training School-Cost action CA21101 COSY "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications", Belgrade, 19th – 22nd September, 2023",
title = "Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone",
pages = "47",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6765"
}

Lazić, A. M., Đorđević, I. S., Radovanović, L. D., Popović, D. M., Rogan, J. R., Trišović, N. P.,& Janjić, G. V.. (2023). Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone. in Book of Abstracts / COST Training School-Cost action CA21101 COSY "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications", Belgrade, 19th – 22nd September, 2023
COST Action CA21101 "COSY"., 47.
https://hdl.handle.net/21.15107/rcub_technorep_6765

Lazić AM, Đorđević IS, Radovanović LD, Popović DM, Rogan JR, Trišović NP, Janjić GV. Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone. in Book of Abstracts / COST Training School-Cost action CA21101 COSY "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications", Belgrade, 19th – 22nd September, 2023. 2023;:47.
https://hdl.handle.net/21.15107/rcub_technorep_6765 .

Lazić, Anita M., Đorđević, Ivana S., Radovanović, Lidija D., Popović, Dragan M., Rogan, Jelena R., Trišović, Nemanja P., Janjić, Goran V., "Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone" in Book of Abstracts / COST Training School-Cost action CA21101 COSY "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications", Belgrade, 19th – 22nd September, 2023 (2023):47,
https://hdl.handle.net/21.15107/rcub_technorep_6765 .

TY  - JOUR
AU  - Suručić, Ljiljana
AU  - Janjić, Goran
AU  - Marković, Bojana
AU  - Tadić, Tamara
AU  - Vuković, Zorica
AU  - Nastasović, Aleksandra
AU  - Onjia, Antonije
PY  - 2023
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6357
AB  - A new magnetic amino-functionalized polymeric sorbent based on glycidyl methacrylate was synthesized and used in the separation of chromium Cr(VI) oxyanions sorption from aqueous solutions in a static batch system. The kinetic and isothermal parameters of the sorption process were determined. The experimental data were best fitted by a pseudo-second-order model with R2 = 0.994 and χ2 = 0.004. The sorption process of Cr(VI) removal by amino-functionalized sorbent was controlled by both intraparticle diffusion and liquid film diffusion. The equilibrium results showed that the sorption process is best described by the Freundlich model, followed closely by the Sips isotherm model, with a maximum sorption capacity of 64 mg/g. Quantum chemical modeling revealed that the sorption sites on the sorbent surface are fragments with diethylenetriamine and aminopropyl silane groups that coated the magnetic nanoparticles. The calculations showed that Cr(VI) oxyanions (Cr2O72−, CrO42− and HCrO4−) bind to both sorption sites, with diethylenetriamine centers slightly favored. The X-ray photoelectron spectroscopy (XPS) spectra demonstrate that the chromium bound to the sorbent in the form of Cr(III), indicating that the Cr(VI) can be converted on the surface of the sorbent to a less harmful form Cr(III) due to the sorbent’s chemical composition.
PB  - MDPI
T2  - Materials
T1  - Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite
IS  - 6
SP  - 2233
VL  - 16
DO  - 10.3390/ma16062233
ER  - 

@article{
author = "Suručić, Ljiljana and Janjić, Goran and Marković, Bojana and Tadić, Tamara and Vuković, Zorica and Nastasović, Aleksandra and Onjia, Antonije",
year = "2023",
abstract = "A new magnetic amino-functionalized polymeric sorbent based on glycidyl methacrylate was synthesized and used in the separation of chromium Cr(VI) oxyanions sorption from aqueous solutions in a static batch system. The kinetic and isothermal parameters of the sorption process were determined. The experimental data were best fitted by a pseudo-second-order model with R2 = 0.994 and χ2 = 0.004. The sorption process of Cr(VI) removal by amino-functionalized sorbent was controlled by both intraparticle diffusion and liquid film diffusion. The equilibrium results showed that the sorption process is best described by the Freundlich model, followed closely by the Sips isotherm model, with a maximum sorption capacity of 64 mg/g. Quantum chemical modeling revealed that the sorption sites on the sorbent surface are fragments with diethylenetriamine and aminopropyl silane groups that coated the magnetic nanoparticles. The calculations showed that Cr(VI) oxyanions (Cr2O72−, CrO42− and HCrO4−) bind to both sorption sites, with diethylenetriamine centers slightly favored. The X-ray photoelectron spectroscopy (XPS) spectra demonstrate that the chromium bound to the sorbent in the form of Cr(III), indicating that the Cr(VI) can be converted on the surface of the sorbent to a less harmful form Cr(III) due to the sorbent’s chemical composition.",
publisher = "MDPI",
journal = "Materials",
title = "Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite",
number = "6",
pages = "2233",
volume = "16",
doi = "10.3390/ma16062233"
}

Suručić, L., Janjić, G., Marković, B., Tadić, T., Vuković, Z., Nastasović, A.,& Onjia, A.. (2023). Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite. in Materials
MDPI., 16(6), 2233.
https://doi.org/10.3390/ma16062233

Suručić L, Janjić G, Marković B, Tadić T, Vuković Z, Nastasović A, Onjia A. Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite. in Materials. 2023;16(6):2233.
doi:10.3390/ma16062233 .

Suručić, Ljiljana, Janjić, Goran, Marković, Bojana, Tadić, Tamara, Vuković, Zorica, Nastasović, Aleksandra, Onjia, Antonije, "Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite" in Materials, 16, no. 6 (2023):2233,
https://doi.org/10.3390/ma16062233 . .

TY  - JOUR
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Valentić, Nataša
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2023
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6504
AB  - The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N-H⋯O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin (1) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins (2-4), were synthesized by the Bucherer-Bergs reaction and their crystal structures were determined by the single crystal X-ray diffraction method. A racemate, racemic hydrate and conglomerate as outcomes of crystallization from racemic solutions were found here. The crystal structures were firstly subjected to Hirshfeld surfaces analysis. The development of hydrogen bonding driven two-dimensional assemblies such as tapes, ribbons and sheets was further analysed using DFT calculations in terms of contribution of dimeric motifs as building blocks, which are associated with the presence of intermolecular interactions. To explore qualitative correlations between intermolecular interactions determining the crystal structures of the investigated compounds and those underlying their biological activity, we performed a docking study on the neuronal voltage gated sodium channels, matrix metalloproteinase 12 and aldose reductase. The supramolecular profiles of the investigated compounds are also maintained in biological systems and as such are responsible for differences in their biological activities.
PB  - Royal Society of Chemistry
T2  - CrystEngComm
T1  - Exploring the supramolecular profile of 5-phenylhydantoins
EP  - 3654
IS  - 25
SP  - 3637
VL  - 25
DO  - 10.1039/d3ce00213f
ER  - 

@article{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Valentić, Nataša and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2023",
abstract = "The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N-H⋯O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin (1) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins (2-4), were synthesized by the Bucherer-Bergs reaction and their crystal structures were determined by the single crystal X-ray diffraction method. A racemate, racemic hydrate and conglomerate as outcomes of crystallization from racemic solutions were found here. The crystal structures were firstly subjected to Hirshfeld surfaces analysis. The development of hydrogen bonding driven two-dimensional assemblies such as tapes, ribbons and sheets was further analysed using DFT calculations in terms of contribution of dimeric motifs as building blocks, which are associated with the presence of intermolecular interactions. To explore qualitative correlations between intermolecular interactions determining the crystal structures of the investigated compounds and those underlying their biological activity, we performed a docking study on the neuronal voltage gated sodium channels, matrix metalloproteinase 12 and aldose reductase. The supramolecular profiles of the investigated compounds are also maintained in biological systems and as such are responsible for differences in their biological activities.",
publisher = "Royal Society of Chemistry",
journal = "CrystEngComm",
title = "Exploring the supramolecular profile of 5-phenylhydantoins",
pages = "3654-3637",
number = "25",
volume = "25",
doi = "10.1039/d3ce00213f"
}

Lazić, A., Radovanović, L., Rogan, J., Valentić, N., Janjić, G., Đorđević, I.,& Trišović, N.. (2023). Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm
Royal Society of Chemistry., 25(25), 3637-3654.
https://doi.org/10.1039/d3ce00213f

Lazić A, Radovanović L, Rogan J, Valentić N, Janjić G, Đorđević I, Trišović N. Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm. 2023;25(25):3637-3654.
doi:10.1039/d3ce00213f .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Valentić, Nataša, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Exploring the supramolecular profile of 5-phenylhydantoins" in CrystEngComm, 25, no. 25 (2023):3637-3654,
https://doi.org/10.1039/d3ce00213f . .

TY  - CONF
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
AU  - Đorđević, Ivana
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6767
AB  - Derivat cikloheksan-5-spirohidantoina (Slika 1) je sintetisan, određena je njegova kristalna
struktura i urađena kvantno-hemijska analiza. Kristalno pakovanje grade mreže
supramolekulskih R6
4
(32) prstenova postavljenih međusobno paralelno, pri čemu se
formiraju linearni kanali. Određene su vrednosti energije intermolekulskih interakcija za
različite dimerne motive dobijene iz kristalne strukture. Uzimajući u razmatranje
prethodno strukturno okarakterisane srodne spirohidantoine [1], dobijena je serija
jedinjenja koja je omogućila procenu uticaja supstituenata na njihovu molekulsku i
kristalnu strukturu.
AB  - A spirohydantoin derivative (Figure 1) was synthesized and its crystal structure was
determined by single crystal X-ray diffraction and analysed by DFT calculations. The
crystal packing is made of supramolecular nets of R6
4
(32) rings linked together to form
stacks that enclose linear channels. The intermolecular interaction energies are quantified
for various dimeric motifs. By including the previously reported structurally-related
spirohydantoins [1], we created a set of compounds that enabled us to evaluate substituent
effects on both molecular and crystal structures.
PB  - Beograd : Srpsko hemijsko društvo
C3  - Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine
T1  - Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina
T1  - Insights into conformational and cristal structure features of selected cyclohexane-5-spirohydantoin derivatives
SP  - 138
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6767
ER  - 

@conference{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja and Đorđević, Ivana",
year = "2022",
abstract = "Derivat cikloheksan-5-spirohidantoina (Slika 1) je sintetisan, određena je njegova kristalna
struktura i urađena kvantno-hemijska analiza. Kristalno pakovanje grade mreže
supramolekulskih R6
4
(32) prstenova postavljenih međusobno paralelno, pri čemu se
formiraju linearni kanali. Određene su vrednosti energije intermolekulskih interakcija za
različite dimerne motive dobijene iz kristalne strukture. Uzimajući u razmatranje
prethodno strukturno okarakterisane srodne spirohidantoine [1], dobijena je serija
jedinjenja koja je omogućila procenu uticaja supstituenata na njihovu molekulsku i
kristalnu strukturu., A spirohydantoin derivative (Figure 1) was synthesized and its crystal structure was
determined by single crystal X-ray diffraction and analysed by DFT calculations. The
crystal packing is made of supramolecular nets of R6
4
(32) rings linked together to form
stacks that enclose linear channels. The intermolecular interaction energies are quantified
for various dimeric motifs. By including the previously reported structurally-related
spirohydantoins [1], we created a set of compounds that enabled us to evaluate substituent
effects on both molecular and crystal structures.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine",
title = "Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina, Insights into conformational and cristal structure features of selected cyclohexane-5-spirohydantoin derivatives",
pages = "138",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6767"
}

Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Trišović, N.,& Đorđević, I.. (2022). Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine
Beograd : Srpsko hemijsko društvo., 138.
https://hdl.handle.net/21.15107/rcub_technorep_6767

Lazić A, Radovanović L, Rogan J, Janjić G, Trišović N, Đorđević I. Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine. 2022;:138.
https://hdl.handle.net/21.15107/rcub_technorep_6767 .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, Đorđević, Ivana, "Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina" in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine (2022):138,
https://hdl.handle.net/21.15107/rcub_technorep_6767 .

TY  - JOUR
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Gak Simić, Kristina
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
AU  - Đorđević, Ivana
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5169
AB  - Two spirohydantoin derivatives, 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-bromobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), were synthesized and analyzed by single crystal X-ray diffraction, DFT and QTAIM calculations. Simple substitution of the benzoyl unit gave rise to different crystal structures. In 1, a parallel stack along the b-axis with alternating perpendicular separation is formed, while in 2 the R46(32) nets are joined together to form stacks which enclose linear channels. Hierarchical development of these crystal structures was analyzed through dimeric motifs associated with the presence of intermolecular interactions. By including the previously reported structurally-related spirohydantoin derivatives, we created a set of structures which enabled us to evaluate substituent effects on their conformational preferences, i.e., widening of the dihedral angle between the hydantoin and substituted benzoyl unit when going from F to Br. A conformational search revealed that the value of the torsion angle N3-C11-C12-C13 can be regarded as a compromise between the extended conjugation between the carbonyl and phenyl group and intramolecular C-H⋯O interaction between these two groups. This intramolecular effect is more pronounced on the torsion angle C2-N3-C11-C12, which defines the relative orientation between the hydantoin ring and the carbonyl bridge. The present work may provide a basis for design of new cyclohexane-5-spirohydantoins with potential for pharmaceutical applications both at the molecular and supramolecular level.
PB  - Royal Society of Chemistry
T2  - CrystEngComm
T1  - Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group
EP  - 4119
IS  - 22
SP  - 4106
VL  - 24
DO  - 10.1039/d2ce00376g
ER  - 

@article{
author = "Lazić, Anita and Radovanović, Lidija and Gak Simić, Kristina and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja and Đorđević, Ivana",
year = "2022",
abstract = "Two spirohydantoin derivatives, 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-bromobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), were synthesized and analyzed by single crystal X-ray diffraction, DFT and QTAIM calculations. Simple substitution of the benzoyl unit gave rise to different crystal structures. In 1, a parallel stack along the b-axis with alternating perpendicular separation is formed, while in 2 the R46(32) nets are joined together to form stacks which enclose linear channels. Hierarchical development of these crystal structures was analyzed through dimeric motifs associated with the presence of intermolecular interactions. By including the previously reported structurally-related spirohydantoin derivatives, we created a set of structures which enabled us to evaluate substituent effects on their conformational preferences, i.e., widening of the dihedral angle between the hydantoin and substituted benzoyl unit when going from F to Br. A conformational search revealed that the value of the torsion angle N3-C11-C12-C13 can be regarded as a compromise between the extended conjugation between the carbonyl and phenyl group and intramolecular C-H⋯O interaction between these two groups. This intramolecular effect is more pronounced on the torsion angle C2-N3-C11-C12, which defines the relative orientation between the hydantoin ring and the carbonyl bridge. The present work may provide a basis for design of new cyclohexane-5-spirohydantoins with potential for pharmaceutical applications both at the molecular and supramolecular level.",
publisher = "Royal Society of Chemistry",
journal = "CrystEngComm",
title = "Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group",
pages = "4119-4106",
number = "22",
volume = "24",
doi = "10.1039/d2ce00376g"
}

Lazić, A., Radovanović, L., Gak Simić, K., Rogan, J., Janjić, G., Trišović, N.,& Đorđević, I.. (2022). Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group. in CrystEngComm
Royal Society of Chemistry., 24(22), 4106-4119.
https://doi.org/10.1039/d2ce00376g

Lazić A, Radovanović L, Gak Simić K, Rogan J, Janjić G, Trišović N, Đorđević I. Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group. in CrystEngComm. 2022;24(22):4106-4119.
doi:10.1039/d2ce00376g .

Lazić, Anita, Radovanović, Lidija, Gak Simić, Kristina, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, Đorđević, Ivana, "Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group" in CrystEngComm, 24, no. 22 (2022):4106-4119,
https://doi.org/10.1039/d2ce00376g . .

TY  - CONF
AU  - Gak Simić, Kristina
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6708
AB  - Sintetisan je derivat cikloheksan-5-spirohidantoina i određena je njegova kristalna
struktura. Hijerarhijski razvoj kristalnog pakovanja diskutovan je sa aspekta
kooperativnosti dimernih motiva koji nastaju preko različitih intermolekulskih
interakcija, i to: jakih N–H···O vodoničnih veza i slabih C–H···O, C–H···Cl i C–H···π
interakcija. Kristalno pakovanje zadržava motiv, koji se obično sreće kod derivata
hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O
vodoničnih veza (slika 1). Specifična strukturna karakteristika jesu paralelni slojevi
duž ac-ravni (slika 2). Pošto ovaj motiv povezuje svaki drugi sloj, rastojanje između
slojeva se naizmenično menja. Naknadna analiza Hiršfeldove površine omogućila je
razradu kvalitativnih i kvantitativnih doprinosa intermolekulskih interakcija
proučavanom kristalnom pakovanju. Kristalografski podaci 3-(4-hlorbenzoil)-1,3-diazaspiro[4.5]dekan-2,4-diona:
C15H15ClN2O3, Mr = 306.7, trikliničan sistem, prostorna grupa P–1, a = 6,2836(13), b =
10,928(2), c = 12,159(2) Å,  = 108,19(3),  = 99,76(3),  = 104,73(3) °, V = 738,4(3) Å3
, Z = 2,
F(000) = 320, ρx = 1,380 g cm–3
, μ(Mo Kα) = 0,270 mm–1
. Utačnjavanje sa F
2
(190 parametara)
dalo je R1 = 0,0821, wR2 = 0,1157, S = 1,031 za sve podatke i R1 = 0,0548 za 2707 uočenih
refleksija sa I ≥ 2σ(I).
AB  - A derivative of cyclohexane-5-spirohydantoin was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of
various dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O, and weaker C–H···O, C–H···Cl and C–H···π interactions. The crystal packing
retained the motif commonly found in hydantoin derivatives where two molecules related by inversion are linked by a pair of N–H∙∙∙O hydrogen bonds (Figure 1). A hallmark structural feature
was a parallel layer arrangement to the ac-plane (Figure 2) with alternating perpendicular separation, whereby this motif connect every second layer. An analysis of the Hirshfeld surface further
elaborated the qualitative and quantitative contributions of intermolecular interactions to the crystal packing. Crystal data for 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione: C15H15ClN2O3, Mr =
306.7, triclinic system, space group P–1, a = 6.2836(13), b = 10.928(2), c = 12.159(2) Å,  =
108.19(3),  = 99.76(3),  = 104.73(3) °, V = 738.4(3) Å3
, Z = 2, F(000) = 320, ρx = 1.380 g cm–3
,
μ(Mo Kα) = 0.270 mm–1
. The refinement on F
2
(190 parameters) yielded R1 = 0.0821, wR2 =
0.1157, S = 1.031 for all data, and R1 = 0.0548 for 2707 observed reflections with I ≥ 2σ(I).
PB  - Beograd : Srpsko kristalografsko društvo
C3  - Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021
T1  - SUPRAMOLEKULSKA ORGANIZACIJA 3-(4-HLORBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA
T1  - SUPRAMOLECULAR ASSOCIATION IN 3-(4-CHLOROBENZOYL)-1,3- DIAZASPIRO[4.5]DECANE-2,4- DIONE
EP  - 25
SP  - 24
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6708
ER  - 

@conference{
author = "Gak Simić, Kristina and Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2021",
abstract = "Sintetisan je derivat cikloheksan-5-spirohidantoina i određena je njegova kristalna
struktura. Hijerarhijski razvoj kristalnog pakovanja diskutovan je sa aspekta
kooperativnosti dimernih motiva koji nastaju preko različitih intermolekulskih
interakcija, i to: jakih N–H···O vodoničnih veza i slabih C–H···O, C–H···Cl i C–H···π
interakcija. Kristalno pakovanje zadržava motiv, koji se obično sreće kod derivata
hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O
vodoničnih veza (slika 1). Specifična strukturna karakteristika jesu paralelni slojevi
duž ac-ravni (slika 2). Pošto ovaj motiv povezuje svaki drugi sloj, rastojanje između
slojeva se naizmenično menja. Naknadna analiza Hiršfeldove površine omogućila je
razradu kvalitativnih i kvantitativnih doprinosa intermolekulskih interakcija
proučavanom kristalnom pakovanju. Kristalografski podaci 3-(4-hlorbenzoil)-1,3-diazaspiro[4.5]dekan-2,4-diona:
C15H15ClN2O3, Mr = 306.7, trikliničan sistem, prostorna grupa P–1, a = 6,2836(13), b =
10,928(2), c = 12,159(2) Å,  = 108,19(3),  = 99,76(3),  = 104,73(3) °, V = 738,4(3) Å3
, Z = 2,
F(000) = 320, ρx = 1,380 g cm–3
, μ(Mo Kα) = 0,270 mm–1
. Utačnjavanje sa F
2
(190 parametara)
dalo je R1 = 0,0821, wR2 = 0,1157, S = 1,031 za sve podatke i R1 = 0,0548 za 2707 uočenih
refleksija sa I ≥ 2σ(I)., A derivative of cyclohexane-5-spirohydantoin was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of
various dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O, and weaker C–H···O, C–H···Cl and C–H···π interactions. The crystal packing
retained the motif commonly found in hydantoin derivatives where two molecules related by inversion are linked by a pair of N–H∙∙∙O hydrogen bonds (Figure 1). A hallmark structural feature
was a parallel layer arrangement to the ac-plane (Figure 2) with alternating perpendicular separation, whereby this motif connect every second layer. An analysis of the Hirshfeld surface further
elaborated the qualitative and quantitative contributions of intermolecular interactions to the crystal packing. Crystal data for 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione: C15H15ClN2O3, Mr =
306.7, triclinic system, space group P–1, a = 6.2836(13), b = 10.928(2), c = 12.159(2) Å,  =
108.19(3),  = 99.76(3),  = 104.73(3) °, V = 738.4(3) Å3
, Z = 2, F(000) = 320, ρx = 1.380 g cm–3
,
μ(Mo Kα) = 0.270 mm–1
. The refinement on F
2
(190 parameters) yielded R1 = 0.0821, wR2 =
0.1157, S = 1.031 for all data, and R1 = 0.0548 for 2707 observed reflections with I ≥ 2σ(I).",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021",
title = "SUPRAMOLEKULSKA ORGANIZACIJA 3-(4-HLORBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA, SUPRAMOLECULAR ASSOCIATION IN 3-(4-CHLOROBENZOYL)-1,3- DIAZASPIRO[4.5]DECANE-2,4- DIONE",
pages = "25-24",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6708"
}

Gak Simić, K., Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Đorđević, I.,& Trišović, N.. (2021). SUPRAMOLEKULSKA ORGANIZACIJA 3-(4-HLORBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA. in Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021
Beograd : Srpsko kristalografsko društvo., 24-25.
https://hdl.handle.net/21.15107/rcub_technorep_6708

Gak Simić K, Lazić A, Radovanović L, Rogan J, Janjić G, Đorđević I, Trišović N. SUPRAMOLEKULSKA ORGANIZACIJA 3-(4-HLORBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA. in Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021. 2021;:24-25.
https://hdl.handle.net/21.15107/rcub_technorep_6708 .

Gak Simić, Kristina, Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "SUPRAMOLEKULSKA ORGANIZACIJA 3-(4-HLORBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA" in Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021 (2021):24-25,
https://hdl.handle.net/21.15107/rcub_technorep_6708 .

TY  - CONF
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Petković-Benazzouz, Marija
AU  - Rogan, Jelena
AU  - Trišović, Nemanja
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6707
AB  - Kristalografska i kvantnohemijska studija, koja je usmerena na proučavanje efekata fluorovan-ja benzoil-grupe vezane za cikloheksan-5-spirohidantoin, pokazala je da aromatični prsten ima najveći afinitet prema cikloheksanskom prstenu (nepolarnim grupama), sa kojim gradi C–H∙∙∙π i paralelne interakcije sa velikim pomakom. Uvođenje atoma fluora na aromatični prsten dovodi do povećanog afiniteta, usled stvaranja dodatnih C–H∙∙∙F interakcija [1]. Dodatno, ova studija je proširena na hlorovane i bromovane derivate. Analizom kristalnog pakovanja četiri derivata spiro-hidantoina (slika) pokazano je da orijentacija aromatičnog prstena, koja je preko rotabilne C(aromatični)–C(karbonilni) veze odvojena od rigidnog spirohidantoinskog jezgra, određuje trodimenzionalnu supramolekulsku arhitekturu. Energijski profil rotabilne veze (slika) jako zavisi od vrste halogenog atoma vezanog za aromatični prsten (X). Najvišu barijeru (najmanju rotacionu slobodu) ima aromatični prsten sa Br atomom (oko 36 kcal/mol), dok najnižu barijeru imaju prstenovi sa vezanim Cl ili F atomom (oko 7 kcal/mol). Izmerene vrednosti torzionog ugla T (slika) u kristalnim stukturama, koji definiše rotabilnost ove veze, odgovaraju minimumima ener-gije na energijskim profilima. Kod ovih orijentacija aromatični prstenovi istovremeno grade C–H...π interakcije sa hidantoinskim prstenom i C–H...O interakciju sa karbonilnom grupom koja premošćuje dva prstena. Na osnovu ovih rezultata može se zaključiti da su orijentacije aro-matičnog prstena određene unutarmolekulskim interakcijama, a ne međumolekulskim interakcija-ma, kao i da su konformacione razlike uzrok razlika u kristalnom pakovanju ovih jedinjenja.
AB  - The crystallographic and quantum chemical study, focused on the effects of fluorination of the benzoyl group bound to the spirohydantoin moiety, showed that the aromatic ring has the highest affinity towards the cyclohexene ring (nonpolar groups), thus forming C–H∙∙∙π and parallel interac-tions at large offset. Introduction of a fluorine atom into the aromatic ring leads to higher affinity, due to formation of additional C–H∙∙∙F interactions [1].
Subsequently, the present study has been extended to chlorinated and brominated derivatives. An analysis of the crystal packaging of four spirohydantoin derivatives (Figure) has shown that the orientation of the aromatic ring, bound to the rigid spirohydantoin moiety by the rotatable C(aromatic)–C(carbonyl) bond, determines the three-dimensional supramolecular architecture. The energy profile of the rotatable bond (Figure) strongly depends on the halogen atom bound to the aromatic ring (X). The highest barrier (the lowest rotational freedom) has been found for the aro-matic ring with the Br atom (36 kcal/mol), while the rings with the Cl or F atom have the lowest barrier (7 kcal/mol). The measured values of the torsion angle T in the crystal structures (Figure), which defines the rotability of the mentioned bond, correspond to the energy minima on the energy profiles. In these orientations, the aromatic ring simultaneously forms C–H...π interactions with the hydantoin ring and C–H...O interaction with the carbonyl spacer group. Based on these results, one can conclude that the orientation of the aromatic ring is defined by intramolecular interactions, not by intermolecular interactions, as well as that the conformational differences further cause differ-ences in the crystal packaging of these compounds.
PB  - Beograd : Srpsko kristalografsko društvo
C3  - Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021
T1  - UTICAJ HALOGENOVANJA AROMATIČNOG PRSTENA NA KONFORMACIJU SPIROHIDANTOINSKIH JEDINJENJA
T1  - INFLUENCE OF HALOGENATION OF AROMATIC RING ON THE CONFORMATION OF SPIROHYDANTOIN COMPOUNDS
EP  - 35
SP  - 34
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6707
ER  - 

@conference{
author = "Janjić, Goran and Đorđević, Ivana and Lazić, Anita and Radovanović, Lidija and Petković-Benazzouz, Marija and Rogan, Jelena and Trišović, Nemanja",
year = "2021",
abstract = "Kristalografska i kvantnohemijska studija, koja je usmerena na proučavanje efekata fluorovan-ja benzoil-grupe vezane za cikloheksan-5-spirohidantoin, pokazala je da aromatični prsten ima najveći afinitet prema cikloheksanskom prstenu (nepolarnim grupama), sa kojim gradi C–H∙∙∙π i paralelne interakcije sa velikim pomakom. Uvođenje atoma fluora na aromatični prsten dovodi do povećanog afiniteta, usled stvaranja dodatnih C–H∙∙∙F interakcija [1]. Dodatno, ova studija je proširena na hlorovane i bromovane derivate. Analizom kristalnog pakovanja četiri derivata spiro-hidantoina (slika) pokazano je da orijentacija aromatičnog prstena, koja je preko rotabilne C(aromatični)–C(karbonilni) veze odvojena od rigidnog spirohidantoinskog jezgra, određuje trodimenzionalnu supramolekulsku arhitekturu. Energijski profil rotabilne veze (slika) jako zavisi od vrste halogenog atoma vezanog za aromatični prsten (X). Najvišu barijeru (najmanju rotacionu slobodu) ima aromatični prsten sa Br atomom (oko 36 kcal/mol), dok najnižu barijeru imaju prstenovi sa vezanim Cl ili F atomom (oko 7 kcal/mol). Izmerene vrednosti torzionog ugla T (slika) u kristalnim stukturama, koji definiše rotabilnost ove veze, odgovaraju minimumima ener-gije na energijskim profilima. Kod ovih orijentacija aromatični prstenovi istovremeno grade C–H...π interakcije sa hidantoinskim prstenom i C–H...O interakciju sa karbonilnom grupom koja premošćuje dva prstena. Na osnovu ovih rezultata može se zaključiti da su orijentacije aro-matičnog prstena određene unutarmolekulskim interakcijama, a ne međumolekulskim interakcija-ma, kao i da su konformacione razlike uzrok razlika u kristalnom pakovanju ovih jedinjenja., The crystallographic and quantum chemical study, focused on the effects of fluorination of the benzoyl group bound to the spirohydantoin moiety, showed that the aromatic ring has the highest affinity towards the cyclohexene ring (nonpolar groups), thus forming C–H∙∙∙π and parallel interac-tions at large offset. Introduction of a fluorine atom into the aromatic ring leads to higher affinity, due to formation of additional C–H∙∙∙F interactions [1].
Subsequently, the present study has been extended to chlorinated and brominated derivatives. An analysis of the crystal packaging of four spirohydantoin derivatives (Figure) has shown that the orientation of the aromatic ring, bound to the rigid spirohydantoin moiety by the rotatable C(aromatic)–C(carbonyl) bond, determines the three-dimensional supramolecular architecture. The energy profile of the rotatable bond (Figure) strongly depends on the halogen atom bound to the aromatic ring (X). The highest barrier (the lowest rotational freedom) has been found for the aro-matic ring with the Br atom (36 kcal/mol), while the rings with the Cl or F atom have the lowest barrier (7 kcal/mol). The measured values of the torsion angle T in the crystal structures (Figure), which defines the rotability of the mentioned bond, correspond to the energy minima on the energy profiles. In these orientations, the aromatic ring simultaneously forms C–H...π interactions with the hydantoin ring and C–H...O interaction with the carbonyl spacer group. Based on these results, one can conclude that the orientation of the aromatic ring is defined by intramolecular interactions, not by intermolecular interactions, as well as that the conformational differences further cause differ-ences in the crystal packaging of these compounds.",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021",
title = "UTICAJ HALOGENOVANJA AROMATIČNOG PRSTENA NA KONFORMACIJU SPIROHIDANTOINSKIH JEDINJENJA, INFLUENCE OF HALOGENATION OF AROMATIC RING ON THE CONFORMATION OF SPIROHYDANTOIN COMPOUNDS",
pages = "35-34",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6707"
}

Janjić, G., Đorđević, I., Lazić, A., Radovanović, L., Petković-Benazzouz, M., Rogan, J.,& Trišović, N.. (2021). UTICAJ HALOGENOVANJA AROMATIČNOG PRSTENA NA KONFORMACIJU SPIROHIDANTOINSKIH JEDINJENJA. in Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021
Beograd : Srpsko kristalografsko društvo., 34-35.
https://hdl.handle.net/21.15107/rcub_technorep_6707

Janjić G, Đorđević I, Lazić A, Radovanović L, Petković-Benazzouz M, Rogan J, Trišović N. UTICAJ HALOGENOVANJA AROMATIČNOG PRSTENA NA KONFORMACIJU SPIROHIDANTOINSKIH JEDINJENJA. in Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021. 2021;:34-35.
https://hdl.handle.net/21.15107/rcub_technorep_6707 .

Janjić, Goran, Đorđević, Ivana, Lazić, Anita, Radovanović, Lidija, Petković-Benazzouz, Marija, Rogan, Jelena, Trišović, Nemanja, "UTICAJ HALOGENOVANJA AROMATIČNOG PRSTENA NA KONFORMACIJU SPIROHIDANTOINSKIH JEDINJENJA" in Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021 (2021):34-35,
https://hdl.handle.net/21.15107/rcub_technorep_6707 .

TY  - CONF
AU  - Lazić, Anita M.
AU  - Đorđević, Ivana S.
AU  - Radovanović, Lidija D.
AU  - Popović, Dragan M.
AU  - Rogan, Jelena R.
AU  - Janjić, Goran V.
AU  - Trišović, Nemanja P.
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6768
AB  - Sintetisan je racemski derivat spirohidantoina, koji poseduje tetralinsku i 4-
metoksibenzil-grupu, a zatim je određena njegova kristalna struktura. Hijerarhijski razvoj
kristalnog pakovanja diskutovan je sa aspekta kooperativnosti homo- i heterohiralnih
dimernih motiva koji odražavaju različite intermolekulske interakcije. Specifična
strukturna karakteristika proučavanog jedinjenja jesu naizmenično postavljeni dvostruki
slojevi. Veliki broj kontaktnih fragmenata u okruženju tetralinske grupe predstavlja
posledicu veće kontaktne površine. Sa druge strane, 4-metoksibenzil-grupa obezbeđuje
veći doprinos ukupnoj stabilizaciji. Što se tiče farmakološkog potencijala proučavanog
jedinjenja, izvršena je simulacija vezivanja molekula za dopaminski receptor D3 i enzim
IRAK 4 (eng. Interleukin-1 Receptor-Associated Kinase 4). Ukupan broj aminokiselinskih
ostataka koji stupaju u interakciju sa 4-metoksibenzil-grupom je nešto veći od broja
aminokiselinskih ostataka u okruženju tetralinske grupe. Usled veće fleksibilnosti,
4-metoksibenzil-grupa se lakše adaptira za uspostavljanje interakcija sa biološkim
ciljevima.
AB  - Sintetisan je racemski derivat spirohidantoina, koji poseduje tetralinsku i 4-
metoksibenzil-grupu, a zatim je određena njegova kristalna struktura. Hijerarhijski razvoj
kristalnog pakovanja diskutovan je sa aspekta kooperativnosti homo- i heterohiralnih
dimernih motiva koji odražavaju različite intermolekulske interakcije. Specifična
strukturna karakteristika proučavanog jedinjenja jesu naizmenično postavljeni dvostruki
slojevi. Veliki broj kontaktnih fragmenata u okruženju tetralinske grupe predstavlja
posledicu veće kontaktne površine. Sa druge strane, 4-metoksibenzil-grupa obezbeđuje
veći doprinos ukupnoj stabilizaciji. Što se tiče farmakološkog potencijala proučavanog
jedinjenja, izvršena je simulacija vezivanja molekula za dopaminski receptor D3 i enzim
IRAK 4 (eng. Interleukin-1 Receptor-Associated Kinase 4). Ukupan broj aminokiselinskih
ostataka koji stupaju u interakciju sa 4-metoksibenzil-grupom je nešto veći od broja
aminokiselinskih ostataka u okruženju tetralinske grupe. Usled veće fleksibilnosti,
4-metoksibenzil-grupa se lakše adaptira za uspostavljanje interakcija sa biološkim
ciljevima.
PB  - Beograd : Srpsko hemijsko društvo
C3  - Kratki izvodi radova ; Knjiga radova / 57. savetovanje Srpskog hemijskog društva, Kragujevac 18. i 19. juni 2021
T1  - Uloga intermolekulskih interakcija u supramolekulskoj organizaciji i biološkom prepoznavanju derivata spirohidantoina
T1  - Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative
SP  - 93
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6768
ER  - 

@conference{
author = "Lazić, Anita M. and Đorđević, Ivana S. and Radovanović, Lidija D. and Popović, Dragan M. and Rogan, Jelena R. and Janjić, Goran V. and Trišović, Nemanja P.",
year = "2021",
abstract = "Sintetisan je racemski derivat spirohidantoina, koji poseduje tetralinsku i 4-
metoksibenzil-grupu, a zatim je određena njegova kristalna struktura. Hijerarhijski razvoj
kristalnog pakovanja diskutovan je sa aspekta kooperativnosti homo- i heterohiralnih
dimernih motiva koji odražavaju različite intermolekulske interakcije. Specifična
strukturna karakteristika proučavanog jedinjenja jesu naizmenično postavljeni dvostruki
slojevi. Veliki broj kontaktnih fragmenata u okruženju tetralinske grupe predstavlja
posledicu veće kontaktne površine. Sa druge strane, 4-metoksibenzil-grupa obezbeđuje
veći doprinos ukupnoj stabilizaciji. Što se tiče farmakološkog potencijala proučavanog
jedinjenja, izvršena je simulacija vezivanja molekula za dopaminski receptor D3 i enzim
IRAK 4 (eng. Interleukin-1 Receptor-Associated Kinase 4). Ukupan broj aminokiselinskih
ostataka koji stupaju u interakciju sa 4-metoksibenzil-grupom je nešto veći od broja
aminokiselinskih ostataka u okruženju tetralinske grupe. Usled veće fleksibilnosti,
4-metoksibenzil-grupa se lakše adaptira za uspostavljanje interakcija sa biološkim
ciljevima., Sintetisan je racemski derivat spirohidantoina, koji poseduje tetralinsku i 4-
metoksibenzil-grupu, a zatim je određena njegova kristalna struktura. Hijerarhijski razvoj
kristalnog pakovanja diskutovan je sa aspekta kooperativnosti homo- i heterohiralnih
dimernih motiva koji odražavaju različite intermolekulske interakcije. Specifična
strukturna karakteristika proučavanog jedinjenja jesu naizmenično postavljeni dvostruki
slojevi. Veliki broj kontaktnih fragmenata u okruženju tetralinske grupe predstavlja
posledicu veće kontaktne površine. Sa druge strane, 4-metoksibenzil-grupa obezbeđuje
veći doprinos ukupnoj stabilizaciji. Što se tiče farmakološkog potencijala proučavanog
jedinjenja, izvršena je simulacija vezivanja molekula za dopaminski receptor D3 i enzim
IRAK 4 (eng. Interleukin-1 Receptor-Associated Kinase 4). Ukupan broj aminokiselinskih
ostataka koji stupaju u interakciju sa 4-metoksibenzil-grupom je nešto veći od broja
aminokiselinskih ostataka u okruženju tetralinske grupe. Usled veće fleksibilnosti,
4-metoksibenzil-grupa se lakše adaptira za uspostavljanje interakcija sa biološkim
ciljevima.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Kratki izvodi radova ; Knjiga radova / 57. savetovanje Srpskog hemijskog društva, Kragujevac 18. i 19. juni 2021",
title = "Uloga intermolekulskih interakcija u supramolekulskoj organizaciji i biološkom prepoznavanju derivata spirohidantoina, Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative",
pages = "93",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6768"
}

Lazić, A. M., Đorđević, I. S., Radovanović, L. D., Popović, D. M., Rogan, J. R., Janjić, G. V.,& Trišović, N. P.. (2021). Uloga intermolekulskih interakcija u supramolekulskoj organizaciji i biološkom prepoznavanju derivata spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 57. savetovanje Srpskog hemijskog društva, Kragujevac 18. i 19. juni 2021
Beograd : Srpsko hemijsko društvo., 93.
https://hdl.handle.net/21.15107/rcub_technorep_6768

Lazić AM, Đorđević IS, Radovanović LD, Popović DM, Rogan JR, Janjić GV, Trišović NP. Uloga intermolekulskih interakcija u supramolekulskoj organizaciji i biološkom prepoznavanju derivata spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 57. savetovanje Srpskog hemijskog društva, Kragujevac 18. i 19. juni 2021. 2021;:93.
https://hdl.handle.net/21.15107/rcub_technorep_6768 .

Lazić, Anita M., Đorđević, Ivana S., Radovanović, Lidija D., Popović, Dragan M., Rogan, Jelena R., Janjić, Goran V., Trišović, Nemanja P., "Uloga intermolekulskih interakcija u supramolekulskoj organizaciji i biološkom prepoznavanju derivata spirohidantoina" in Kratki izvodi radova ; Knjiga radova / 57. savetovanje Srpskog hemijskog društva, Kragujevac 18. i 19. juni 2021 (2021):93,
https://hdl.handle.net/21.15107/rcub_technorep_6768 .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Đorđević, Ivana S.
AU  - Radovanović, Lidija D.
AU  - Popović, Dragan M.
AU  - Rogan, Jelena R.
AU  - Janjić, Goran V.
AU  - Trišović, Nemanja P.
PY  - 2020
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4504
AB  - A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.
PB  - Wiley-VCH Verlag
T2  - Chempluschem
T1  - Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions
EP  - 1232
IS  - 6
SP  - 1220
VL  - 85
DO  - 10.1002/cplu.202000273
ER  - 

@article{
author = "Lazić, Anita M. and Đorđević, Ivana S. and Radovanović, Lidija D. and Popović, Dragan M. and Rogan, Jelena R. and Janjić, Goran V. and Trišović, Nemanja P.",
year = "2020",
abstract = "A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.",
publisher = "Wiley-VCH Verlag",
journal = "Chempluschem",
title = "Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions",
pages = "1232-1220",
number = "6",
volume = "85",
doi = "10.1002/cplu.202000273"
}

Lazić, A. M., Đorđević, I. S., Radovanović, L. D., Popović, D. M., Rogan, J. R., Janjić, G. V.,& Trišović, N. P.. (2020). Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions. in Chempluschem
Wiley-VCH Verlag., 85(6), 1220-1232.
https://doi.org/10.1002/cplu.202000273

Lazić AM, Đorđević IS, Radovanović LD, Popović DM, Rogan JR, Janjić GV, Trišović NP. Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions. in Chempluschem. 2020;85(6):1220-1232.
doi:10.1002/cplu.202000273 .

Lazić, Anita M., Đorđević, Ivana S., Radovanović, Lidija D., Popović, Dragan M., Rogan, Jelena R., Janjić, Goran V., Trišović, Nemanja P., "Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions" in Chempluschem, 85, no. 6 (2020):1220-1232,
https://doi.org/10.1002/cplu.202000273 . .

TY  - JOUR
AU  - Janjić, Goran
AU  - Jelić, Stefan
AU  - Trišović, Nemanja
AU  - Popović, Dragan
AU  - Đorđević, Ivana
AU  - Milčić, Miloš
PY  - 2020
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4527
AB  - Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.
PB  - Amer Chemical Soc, Washington
T2  - Crystal Growth & Design
T1  - New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures
EP  - 2951
IS  - 5
SP  - 2943
VL  - 20
DO  - 10.1021/acs.cgd.9b01565
ER  - 

@article{
author = "Janjić, Goran and Jelić, Stefan and Trišović, Nemanja and Popović, Dragan and Đorđević, Ivana and Milčić, Miloš",
year = "2020",
abstract = "Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.",
publisher = "Amer Chemical Soc, Washington",
journal = "Crystal Growth & Design",
title = "New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures",
pages = "2951-2943",
number = "5",
volume = "20",
doi = "10.1021/acs.cgd.9b01565"
}

Janjić, G., Jelić, S., Trišović, N., Popović, D., Đorđević, I.,& Milčić, M.. (2020). New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth & Design
Amer Chemical Soc, Washington., 20(5), 2943-2951.
https://doi.org/10.1021/acs.cgd.9b01565

Janjić G, Jelić S, Trišović N, Popović D, Đorđević I, Milčić M. New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth & Design. 2020;20(5):2943-2951.
doi:10.1021/acs.cgd.9b01565 .

Janjić, Goran, Jelić, Stefan, Trišović, Nemanja, Popović, Dragan, Đorđević, Ivana, Milčić, Miloš, "New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures" in Crystal Growth & Design, 20, no. 5 (2020):2943-2951,
https://doi.org/10.1021/acs.cgd.9b01565 . .

TY  - CONF
AU  - Trišović, Nemanja
AU  - Jelić, Stefan
AU  - Popović, Dragan
AU  - Đorđević, Ivana
AU  - Milčić, Miloš
AU  - Janjić, Goran
PY  - 2020
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4408
AB  - The results of the crystallographic analysis in combination with quantum chemical calculations have shown that fluorination of organic compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of the groups in their neighbourhood1 . The establishment of F∙∙∙F interactions causes the electron density to shift towards the area of F∙∙∙F contact, thus creating a new region with a higher negative potential and the more pronounced accepting ability. This new region has a larger surface area and it is able to form simultaneous interactions with species from the crystal environment. This compensates the reduction of the accepting capacity of the groups in the neigbourhood of the interacting F atoms. Taking into account the formation of this new region, not only the abundance of F∙∙∙F interactions in the crystal structures (the second largest group of interactions), but also a large number of structures with F∙∙∙O interactions (third largest group of interactions) can be explained. Only the C–H∙∙∙F interactions are more numerous than F∙∙∙F interactions, indicating an increased affinity of fluorinated compounds for non-polar groups.
PB  - Commission on Quantum Crystallography of IUCr
C3  - Book of Abstracts - Quantum Crystallography Online Meeting 2020, QCrOM2020
T1  - Fluorination as a Driving Force in Crystal Structures
SP  - 35
UR  - https://hdl.handle.net/21.15107/rcub_technorep_4408
ER  - 

@conference{
author = "Trišović, Nemanja and Jelić, Stefan and Popović, Dragan and Đorđević, Ivana and Milčić, Miloš and Janjić, Goran",
year = "2020",
abstract = "The results of the crystallographic analysis in combination with quantum chemical calculations have shown that fluorination of organic compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of the groups in their neighbourhood1 . The establishment of F∙∙∙F interactions causes the electron density to shift towards the area of F∙∙∙F contact, thus creating a new region with a higher negative potential and the more pronounced accepting ability. This new region has a larger surface area and it is able to form simultaneous interactions with species from the crystal environment. This compensates the reduction of the accepting capacity of the groups in the neigbourhood of the interacting F atoms. Taking into account the formation of this new region, not only the abundance of F∙∙∙F interactions in the crystal structures (the second largest group of interactions), but also a large number of structures with F∙∙∙O interactions (third largest group of interactions) can be explained. Only the C–H∙∙∙F interactions are more numerous than F∙∙∙F interactions, indicating an increased affinity of fluorinated compounds for non-polar groups.",
publisher = "Commission on Quantum Crystallography of IUCr",
journal = "Book of Abstracts - Quantum Crystallography Online Meeting 2020, QCrOM2020",
title = "Fluorination as a Driving Force in Crystal Structures",
pages = "35",
url = "https://hdl.handle.net/21.15107/rcub_technorep_4408"
}

Trišović, N., Jelić, S., Popović, D., Đorđević, I., Milčić, M.,& Janjić, G.. (2020). Fluorination as a Driving Force in Crystal Structures. in Book of Abstracts - Quantum Crystallography Online Meeting 2020, QCrOM2020
Commission on Quantum Crystallography of IUCr., 35.
https://hdl.handle.net/21.15107/rcub_technorep_4408

Trišović N, Jelić S, Popović D, Đorđević I, Milčić M, Janjić G. Fluorination as a Driving Force in Crystal Structures. in Book of Abstracts - Quantum Crystallography Online Meeting 2020, QCrOM2020. 2020;:35.
https://hdl.handle.net/21.15107/rcub_technorep_4408 .

Trišović, Nemanja, Jelić, Stefan, Popović, Dragan, Đorđević, Ivana, Milčić, Miloš, Janjić, Goran, "Fluorination as a Driving Force in Crystal Structures" in Book of Abstracts - Quantum Crystallography Online Meeting 2020, QCrOM2020 (2020):35,
https://hdl.handle.net/21.15107/rcub_technorep_4408 .

TY  - CONF
AU  - Đorđević, Ivana
AU  - Janjić, Goran
AU  - Lazić, Anita
AU  - Gak, Kristina
AU  - Valentić, Nataša
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6705
AB  - Nekovalentne interakcije imaju značajnu ulogu u formiranju supramolekulskog
kristalnog pakovanja molekula. Interakcije koje uključuju atome halogena obezbeđuju
slabo, ali visoko usmerenu kontrolu pakovanja molekula u čvrstom stanju. Uvođenje
F-atoma može dovesti do značajnih promena u 2D ili 3D strukturama [1], povećanja
stabilnosti biomolekula [2] ili poboljšanja dizajna lekova [3]. Da bi se ispitao efekat
supstitucije H-atoma F-atomom, sintetisana su i strukturno okarakterisana dva derivata
hidantoina: C15H16N2O3 (1) i C15H15N2O3F (2) (slika).
Analiza kristalnih pakovanja 1 i 2 pokazala je da su
NH…O i CH…O vodonične veze najbrojnije. U strukturi
2 se zbog fluorovanja povećava broj interakcija
cikloheksilnog (Ch) i fenil-grupe (Ph) prstena (CH…π
interakcije), kao i između dva Ph prstena (π-π
interakcije). Kvantno-hemijski proračuni na model
sistemima koji predstavljaju dimere derivata hidantoina
i izolovanih cikličnih jedinjenja, pokazali su da
fluorovanje utiče na stvaranje jačih CH…π i π-π
interakcija. Atom F u 2 učestvuje u formiranju tri
CH…F i jedne F…F interakcije, što je u saglasnosti sa
rezultatima Kembridžke baze podataka, koji su pokazali
da su najbrojnije CH…F i F…F interakcije, a njihova
jačina dostiže vrednost 2 kcal∙mol–1.
Kristalogafski podaci: 1, P–1, a = 6,3079(13),
b = 10,573(2), c = 11,415(2) Å, α = 67,21(3), β = 78,84(3),
γ = 76,16(3)°, R1 = 6,06%; 2, P–1, a = 5,9981(12), b =
11,148(2), c = 12,073(2) Å, α = 108,98(3), β = 101,57(3),
γ = 105,27(3)°, R1 = 4,82%.
AB  - Non-covalent interactions have a significant role in supramolecular crystal packings
of the molecules. Halogen interactions provide weak but highly directed control of the
packing of molecules in the solid state. Introduction of F atom can leads to significant
differences in 2D or 3D structures [1], higher structural stability of biomolecules [2] or
improve drug design [3]. In order to examine the substitution effect of H atom with F
atom, two hydantoin derivatives were synthesized and structurally characterized:
C15H16N2O3 (1) i C15H15N2O3F (2) (Figure).
Crystallographic analysis of 1 and 2 showed that
NH…O and CH…O hydrogen bonds are the most numerous
in their crystal packings. Due to fluoridation in 2, the number of interactions among cyclohexyl (Ch) and phenyl ring
(Ph) rings (CH…π interactions), as well as among two Ph
rings (π-π interactions) is increased. Quantum-chemical
calculations on the model systems presented by dimmers
of hydantoin derivatives and isolated cyclic compounds,
verified that fluoridation caused the formation of stronger
CH…π and π-π interactions. The F atom in 2 is involved in
three CH…F and one F…F interactions, which is in agreement with the results from the Cambridge Structural Database, which have shown that CH…F and F…F interactions
are the most numerous, and their strength reaches the value
of 2 kcal∙mol–1.
Crystallographic data: 1, P–1, a = 6.3079(13),
b = 10.573(2), c = 11.415(2) Å, α = 67.21(3), β = 78.84(3),
γ = 76.16(3)°, R1 = 6.06%; 2, P–1, a = 5.9981(12),
b = 11.148(2), c = 12.073(2) Å, α = 108.98(3), β = 101.57(3), γ = 105.27(3)°, R1 = 4.82%.
PB  - Beograd : Srpsko kristalografsko društvo
C3  - Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019
T1  - ULOGA NEKOVALENTNIH INTERAKCIJA FLUORA U PAKOVANJU MOTIVA: ANALIZA KRISTALOGRAFSKIH PODATAKA I KVANTNO-HEMIJSKI PRORAČUNI
T1  - THE ROLE OF NON-COVALENT FLUORINE INTERACTIONS IN PACKING MOTIFS: CRYSTALLOGRAPHIC DATA ANALYSIS AND QUANTUM CHEMICAL CALCULATIONS
EP  - 39
SP  - 38
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6705
ER  - 

@conference{
author = "Đorđević, Ivana and Janjić, Goran and Lazić, Anita and Gak, Kristina and Valentić, Nataša and Trišović, Nemanja and Radovanović, Lidija and Rogan, Jelena",
year = "2019",
abstract = "Nekovalentne interakcije imaju značajnu ulogu u formiranju supramolekulskog
kristalnog pakovanja molekula. Interakcije koje uključuju atome halogena obezbeđuju
slabo, ali visoko usmerenu kontrolu pakovanja molekula u čvrstom stanju. Uvođenje
F-atoma može dovesti do značajnih promena u 2D ili 3D strukturama [1], povećanja
stabilnosti biomolekula [2] ili poboljšanja dizajna lekova [3]. Da bi se ispitao efekat
supstitucije H-atoma F-atomom, sintetisana su i strukturno okarakterisana dva derivata
hidantoina: C15H16N2O3 (1) i C15H15N2O3F (2) (slika).
Analiza kristalnih pakovanja 1 i 2 pokazala je da su
NH…O i CH…O vodonične veze najbrojnije. U strukturi
2 se zbog fluorovanja povećava broj interakcija
cikloheksilnog (Ch) i fenil-grupe (Ph) prstena (CH…π
interakcije), kao i između dva Ph prstena (π-π
interakcije). Kvantno-hemijski proračuni na model
sistemima koji predstavljaju dimere derivata hidantoina
i izolovanih cikličnih jedinjenja, pokazali su da
fluorovanje utiče na stvaranje jačih CH…π i π-π
interakcija. Atom F u 2 učestvuje u formiranju tri
CH…F i jedne F…F interakcije, što je u saglasnosti sa
rezultatima Kembridžke baze podataka, koji su pokazali
da su najbrojnije CH…F i F…F interakcije, a njihova
jačina dostiže vrednost 2 kcal∙mol–1.
Kristalogafski podaci: 1, P–1, a = 6,3079(13),
b = 10,573(2), c = 11,415(2) Å, α = 67,21(3), β = 78,84(3),
γ = 76,16(3)°, R1 = 6,06%; 2, P–1, a = 5,9981(12), b =
11,148(2), c = 12,073(2) Å, α = 108,98(3), β = 101,57(3),
γ = 105,27(3)°, R1 = 4,82%., Non-covalent interactions have a significant role in supramolecular crystal packings
of the molecules. Halogen interactions provide weak but highly directed control of the
packing of molecules in the solid state. Introduction of F atom can leads to significant
differences in 2D or 3D structures [1], higher structural stability of biomolecules [2] or
improve drug design [3]. In order to examine the substitution effect of H atom with F
atom, two hydantoin derivatives were synthesized and structurally characterized:
C15H16N2O3 (1) i C15H15N2O3F (2) (Figure).
Crystallographic analysis of 1 and 2 showed that
NH…O and CH…O hydrogen bonds are the most numerous
in their crystal packings. Due to fluoridation in 2, the number of interactions among cyclohexyl (Ch) and phenyl ring
(Ph) rings (CH…π interactions), as well as among two Ph
rings (π-π interactions) is increased. Quantum-chemical
calculations on the model systems presented by dimmers
of hydantoin derivatives and isolated cyclic compounds,
verified that fluoridation caused the formation of stronger
CH…π and π-π interactions. The F atom in 2 is involved in
three CH…F and one F…F interactions, which is in agreement with the results from the Cambridge Structural Database, which have shown that CH…F and F…F interactions
are the most numerous, and their strength reaches the value
of 2 kcal∙mol–1.
Crystallographic data: 1, P–1, a = 6.3079(13),
b = 10.573(2), c = 11.415(2) Å, α = 67.21(3), β = 78.84(3),
γ = 76.16(3)°, R1 = 6.06%; 2, P–1, a = 5.9981(12),
b = 11.148(2), c = 12.073(2) Å, α = 108.98(3), β = 101.57(3), γ = 105.27(3)°, R1 = 4.82%.",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019",
title = "ULOGA NEKOVALENTNIH INTERAKCIJA FLUORA U PAKOVANJU MOTIVA: ANALIZA KRISTALOGRAFSKIH PODATAKA I KVANTNO-HEMIJSKI PRORAČUNI, THE ROLE OF NON-COVALENT FLUORINE INTERACTIONS IN PACKING MOTIFS: CRYSTALLOGRAPHIC DATA ANALYSIS AND QUANTUM CHEMICAL CALCULATIONS",
pages = "39-38",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6705"
}

Đorđević, I., Janjić, G., Lazić, A., Gak, K., Valentić, N., Trišović, N., Radovanović, L.,& Rogan, J.. (2019). ULOGA NEKOVALENTNIH INTERAKCIJA FLUORA U PAKOVANJU MOTIVA: ANALIZA KRISTALOGRAFSKIH PODATAKA I KVANTNO-HEMIJSKI PRORAČUNI. in Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019
Beograd : Srpsko kristalografsko društvo., 38-39.
https://hdl.handle.net/21.15107/rcub_technorep_6705

Đorđević I, Janjić G, Lazić A, Gak K, Valentić N, Trišović N, Radovanović L, Rogan J. ULOGA NEKOVALENTNIH INTERAKCIJA FLUORA U PAKOVANJU MOTIVA: ANALIZA KRISTALOGRAFSKIH PODATAKA I KVANTNO-HEMIJSKI PRORAČUNI. in Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019. 2019;:38-39.
https://hdl.handle.net/21.15107/rcub_technorep_6705 .

Đorđević, Ivana, Janjić, Goran, Lazić, Anita, Gak, Kristina, Valentić, Nataša, Trišović, Nemanja, Radovanović, Lidija, Rogan, Jelena, "ULOGA NEKOVALENTNIH INTERAKCIJA FLUORA U PAKOVANJU MOTIVA: ANALIZA KRISTALOGRAFSKIH PODATAKA I KVANTNO-HEMIJSKI PRORAČUNI" in Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019 (2019):38-39,
https://hdl.handle.net/21.15107/rcub_technorep_6705 .

TY  - JOUR
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija
AU  - Janjić, Goran V.
AU  - Jelić, Stefan T.
AU  - Rogan, Jelena
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4244
AB  - A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N-H center dot center dot center dot O hydrogen bonds, which further self-organize through pairs of C-H center dot center dot center dot O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.
PB  - American Chemical Society (ACS)
T2  - Crystal Growth & Design
T1  - Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study
EP  - 2174
IS  - 4
SP  - 2163
VL  - 19
DO  - 10.1021/acs.cgd.8b01776
ER  - 

@article{
author = "Trišović, Nemanja and Radovanović, Lidija and Janjić, Goran V. and Jelić, Stefan T. and Rogan, Jelena",
year = "2019",
abstract = "A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N-H center dot center dot center dot O hydrogen bonds, which further self-organize through pairs of C-H center dot center dot center dot O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.",
publisher = "American Chemical Society (ACS)",
journal = "Crystal Growth & Design",
title = "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study",
pages = "2174-2163",
number = "4",
volume = "19",
doi = "10.1021/acs.cgd.8b01776"
}

Trišović, N., Radovanović, L., Janjić, G. V., Jelić, S. T.,& Rogan, J.. (2019). Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design
American Chemical Society (ACS)., 19(4), 2163-2174.
https://doi.org/10.1021/acs.cgd.8b01776

Trišović N, Radovanović L, Janjić GV, Jelić ST, Rogan J. Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design. 2019;19(4):2163-2174.
doi:10.1021/acs.cgd.8b01776 .

Trišović, Nemanja, Radovanović, Lidija, Janjić, Goran V., Jelić, Stefan T., Rogan, Jelena, "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study" in Crystal Growth & Design, 19, no. 4 (2019):2163-2174,
https://doi.org/10.1021/acs.cgd.8b01776 . .

TY  - JOUR
AU  - Suručić, Ljiljana T.
AU  - Nastasović, Aleksandra
AU  - Rakić, Aleksandra
AU  - Onjia, Antonije
AU  - Popović, Aleksandar R.
AU  - Janjić, Goran
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4197
PB  - 5th World Congress on Mechanical, Chemical, and Material Engineering, MCM 2019
T2  - Proceedings of the World Congress on Mechanical, Chemical, and Material Engineering
T1  - Comparative study of W(VI) and Cr(VI) oxyanions binding ability with magnetic polymer nanocomposite
DO  - 10.11159/iccpe19.125
ER  - 

@article{
author = "Suručić, Ljiljana T. and Nastasović, Aleksandra and Rakić, Aleksandra and Onjia, Antonije and Popović, Aleksandar R. and Janjić, Goran",
year = "2019",
publisher = "5th World Congress on Mechanical, Chemical, and Material Engineering, MCM 2019",
journal = "Proceedings of the World Congress on Mechanical, Chemical, and Material Engineering",
title = "Comparative study of W(VI) and Cr(VI) oxyanions binding ability with magnetic polymer nanocomposite",
doi = "10.11159/iccpe19.125"
}

Suručić, L. T., Nastasović, A., Rakić, A., Onjia, A., Popović, A. R.,& Janjić, G.. (2019). Comparative study of W(VI) and Cr(VI) oxyanions binding ability with magnetic polymer nanocomposite. in Proceedings of the World Congress on Mechanical, Chemical, and Material Engineering
5th World Congress on Mechanical, Chemical, and Material Engineering, MCM 2019..
https://doi.org/10.11159/iccpe19.125

Suručić LT, Nastasović A, Rakić A, Onjia A, Popović AR, Janjić G. Comparative study of W(VI) and Cr(VI) oxyanions binding ability with magnetic polymer nanocomposite. in Proceedings of the World Congress on Mechanical, Chemical, and Material Engineering. 2019;.
doi:10.11159/iccpe19.125 .

Suručić, Ljiljana T., Nastasović, Aleksandra, Rakić, Aleksandra, Onjia, Antonije, Popović, Aleksandar R., Janjić, Goran, "Comparative study of W(VI) and Cr(VI) oxyanions binding ability with magnetic polymer nanocomposite" in Proceedings of the World Congress on Mechanical, Chemical, and Material Engineering (2019),
https://doi.org/10.11159/iccpe19.125 . .

TY  - JOUR
AU  - Suručić, Ljiljana T.
AU  - Janjić, Goran
AU  - Rakić, Aleksandra
AU  - Nastasović, Aleksandra
AU  - Popović, Aleksandar R.
AU  - Milčić, Miloš
AU  - Onjia, Antonije
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4217
AB  - With regard to the harmful effects of heavy metals on human health and the environment, the demand for synthesis and investigation of macromolecules with large capacity of harmful substances sorption is ever greater. Quantum-chemical methods may be applied in structural modeling, prediction, and characterization of such molecules and reactions. Sorption of metal ions (Cu2+, Cd2+, Co2+, and Ni2+) to triethylenetetramine-functionalized copolymer poly(GMA-co-EGDMA)-teta was successfully modeled by quantum chemical calculations, at the B3LYP//6-311++G**/lanl2dz level. Optimized structures of metal complexes were used for calculation of real binding energy of metal ion within the complex (Er). Solvent and hydrolyzation effects were essential for obtaining the objective values. Solvent effect was included in Er by using the total solvation energy for reaction of formation of tetaOH complex (Es1, the first approach) or by using dehydration energy of free metal ion (Es2, the second approach). Experimental results were confirmed in our theoretical analyses (using the second approach).
PB  - Springer, New York
T2  - Journal of Molecular Modeling
T1  - Theoretical modeling of sorption of metal ions on amino-functionalized macroporous copolymer in aqueous solution
IS  - 6
VL  - 25
DO  - 10.1007/s00894-019-4053-0
ER  - 

@article{
author = "Suručić, Ljiljana T. and Janjić, Goran and Rakić, Aleksandra and Nastasović, Aleksandra and Popović, Aleksandar R. and Milčić, Miloš and Onjia, Antonije",
year = "2019",
abstract = "With regard to the harmful effects of heavy metals on human health and the environment, the demand for synthesis and investigation of macromolecules with large capacity of harmful substances sorption is ever greater. Quantum-chemical methods may be applied in structural modeling, prediction, and characterization of such molecules and reactions. Sorption of metal ions (Cu2+, Cd2+, Co2+, and Ni2+) to triethylenetetramine-functionalized copolymer poly(GMA-co-EGDMA)-teta was successfully modeled by quantum chemical calculations, at the B3LYP//6-311++G**/lanl2dz level. Optimized structures of metal complexes were used for calculation of real binding energy of metal ion within the complex (Er). Solvent and hydrolyzation effects were essential for obtaining the objective values. Solvent effect was included in Er by using the total solvation energy for reaction of formation of tetaOH complex (Es1, the first approach) or by using dehydration energy of free metal ion (Es2, the second approach). Experimental results were confirmed in our theoretical analyses (using the second approach).",
publisher = "Springer, New York",
journal = "Journal of Molecular Modeling",
title = "Theoretical modeling of sorption of metal ions on amino-functionalized macroporous copolymer in aqueous solution",
number = "6",
volume = "25",
doi = "10.1007/s00894-019-4053-0"
}

Suručić, L. T., Janjić, G., Rakić, A., Nastasović, A., Popović, A. R., Milčić, M.,& Onjia, A.. (2019). Theoretical modeling of sorption of metal ions on amino-functionalized macroporous copolymer in aqueous solution. in Journal of Molecular Modeling
Springer, New York., 25(6).
https://doi.org/10.1007/s00894-019-4053-0

Suručić LT, Janjić G, Rakić A, Nastasović A, Popović AR, Milčić M, Onjia A. Theoretical modeling of sorption of metal ions on amino-functionalized macroporous copolymer in aqueous solution. in Journal of Molecular Modeling. 2019;25(6).
doi:10.1007/s00894-019-4053-0 .

Suručić, Ljiljana T., Janjić, Goran, Rakić, Aleksandra, Nastasović, Aleksandra, Popović, Aleksandar R., Milčić, Miloš, Onjia, Antonije, "Theoretical modeling of sorption of metal ions on amino-functionalized macroporous copolymer in aqueous solution" in Journal of Molecular Modeling, 25, no. 6 (2019),
https://doi.org/10.1007/s00894-019-4053-0 . .

TY  - JOUR
AU  - Suručić, Ljiljana T.
AU  - Nastasović, Aleksandra
AU  - Onjia, Antonije
AU  - Janjić, Goran
AU  - Rakić, Aleksandra
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4208
AB  - Polymer-based, highly porous nanocomposites with functionalized ligands attached to the core structure are extremely efficient in the detection, removal and recovery of metals through the process of sorption. Quantum-chemical models could be helpful for sorption process analyses. The sorption of Cu(II) ions by amino-functionalized chelating macroporous copolymers poly(GMA-co-EGDMA)-amine and sorption selectivity of the subject copolymers, ethylenediamine (en), diethylenetriamine (dien) and triethylenetetramine (trien), were successfully modelled by quantum chemical calculations. Considering the crystal structures from CSD and experimental conditions during the formation of metal complexes, the most frequent mononuclear complexes are those with the tetradentate teta ligand, while binuclear complexes are formed when the metal ion is in large excess. Although the en-copolymer was the most effective functionalized one, higher maximum sorption capacities (Q(max)) were observed for the dien- and trien-copolymers, due to their abilities to form binuclear complexes. The enthalpy term has the greatest contribution to the total Gibbs energy change of reaction for the formation of mononuclear Cu(II) complexes (Delta G(aq)), while the solvation energy of the reaction has the greatest contribution in the formation of binuclear complexes. The results of the study indicate that small amines with the ability to form binuclear complex are the best choice for functionalization of the considered copolymer.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Design of an amino-functionalized chelating macroporous copolymer poly(GMA-co-EGDMA) for the sorption of Cu(II) ions
EP  - 1404
IS  - 12
SP  - 1391
VL  - 84
DO  - 10.2298/JSC190125031S
ER  - 

@article{
author = "Suručić, Ljiljana T. and Nastasović, Aleksandra and Onjia, Antonije and Janjić, Goran and Rakić, Aleksandra",
year = "2019",
abstract = "Polymer-based, highly porous nanocomposites with functionalized ligands attached to the core structure are extremely efficient in the detection, removal and recovery of metals through the process of sorption. Quantum-chemical models could be helpful for sorption process analyses. The sorption of Cu(II) ions by amino-functionalized chelating macroporous copolymers poly(GMA-co-EGDMA)-amine and sorption selectivity of the subject copolymers, ethylenediamine (en), diethylenetriamine (dien) and triethylenetetramine (trien), were successfully modelled by quantum chemical calculations. Considering the crystal structures from CSD and experimental conditions during the formation of metal complexes, the most frequent mononuclear complexes are those with the tetradentate teta ligand, while binuclear complexes are formed when the metal ion is in large excess. Although the en-copolymer was the most effective functionalized one, higher maximum sorption capacities (Q(max)) were observed for the dien- and trien-copolymers, due to their abilities to form binuclear complexes. The enthalpy term has the greatest contribution to the total Gibbs energy change of reaction for the formation of mononuclear Cu(II) complexes (Delta G(aq)), while the solvation energy of the reaction has the greatest contribution in the formation of binuclear complexes. The results of the study indicate that small amines with the ability to form binuclear complex are the best choice for functionalization of the considered copolymer.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Design of an amino-functionalized chelating macroporous copolymer poly(GMA-co-EGDMA) for the sorption of Cu(II) ions",
pages = "1404-1391",
number = "12",
volume = "84",
doi = "10.2298/JSC190125031S"
}

Suručić, L. T., Nastasović, A., Onjia, A., Janjić, G.,& Rakić, A.. (2019). Design of an amino-functionalized chelating macroporous copolymer poly(GMA-co-EGDMA) for the sorption of Cu(II) ions. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 84(12), 1391-1404.
https://doi.org/10.2298/JSC190125031S

Suručić LT, Nastasović A, Onjia A, Janjić G, Rakić A. Design of an amino-functionalized chelating macroporous copolymer poly(GMA-co-EGDMA) for the sorption of Cu(II) ions. in Journal of the Serbian Chemical Society. 2019;84(12):1391-1404.
doi:10.2298/JSC190125031S .

Suručić, Ljiljana T., Nastasović, Aleksandra, Onjia, Antonije, Janjić, Goran, Rakić, Aleksandra, "Design of an amino-functionalized chelating macroporous copolymer poly(GMA-co-EGDMA) for the sorption of Cu(II) ions" in Journal of the Serbian Chemical Society, 84, no. 12 (2019):1391-1404,
https://doi.org/10.2298/JSC190125031S . .