TY  - JOUR
AU  - Gak Simić, Kristina
AU  - Đorđević, Ivana
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Petković-Benazzouz, Marija
AU  - Rogan, Jelena
AU  - Trišović, Nemanja
AU  - Janjić, Goran
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4888
AB  - The quantitative assessment of intermolecular interactions and their cooperative effects has been performed in spirohydantoin-based model compounds, 3-benzoyl-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-fluorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), through single crystal X-ray crystallography and quantum chemical studies. In both crystal structures, molecules generate the same hydrogen-bonded centrosymmetric R22(8) synthon. The extended supramolecular architectures depend on the C-HMIDLINE HORIZONTAL ELLIPSISO, C-HMIDLINE HORIZONTAL ELLIPSIS pi, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HMIDLINE HORIZONTAL ELLIPSISF interaction in the case of 2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FMIDLINE HORIZONTAL ELLIPSISF interaction in the crystal structure of 2 results in a new region with a larger surface area and a higher negative potential in comparison to the individual fluorine atoms. Establishment of this interaction leads to strengthening of the interaction of one of the fluorine atoms with a third molecule from the environment which does not interact with both of them. When this third molecule interacts with both fluorine atoms simultaneously, the calculations have shown that the effect of strengthening of the individual interactions due to formation of the FMIDLINE HORIZONTAL ELLIPSISF interaction is absent.
T2  - CrystEngComm
T1  - On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives
EP  - 2622
IS  - 13
SP  - 2606
VL  - 23
DO  - 10.1039/d0ce01841d
ER  - 

@article{
author = "Gak Simić, Kristina and Đorđević, Ivana and Lazić, Anita and Radovanović, Lidija and Petković-Benazzouz, Marija and Rogan, Jelena and Trišović, Nemanja and Janjić, Goran",
year = "2021",
abstract = "The quantitative assessment of intermolecular interactions and their cooperative effects has been performed in spirohydantoin-based model compounds, 3-benzoyl-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-fluorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), through single crystal X-ray crystallography and quantum chemical studies. In both crystal structures, molecules generate the same hydrogen-bonded centrosymmetric R22(8) synthon. The extended supramolecular architectures depend on the C-HMIDLINE HORIZONTAL ELLIPSISO, C-HMIDLINE HORIZONTAL ELLIPSIS pi, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HMIDLINE HORIZONTAL ELLIPSISF interaction in the case of 2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FMIDLINE HORIZONTAL ELLIPSISF interaction in the crystal structure of 2 results in a new region with a larger surface area and a higher negative potential in comparison to the individual fluorine atoms. Establishment of this interaction leads to strengthening of the interaction of one of the fluorine atoms with a third molecule from the environment which does not interact with both of them. When this third molecule interacts with both fluorine atoms simultaneously, the calculations have shown that the effect of strengthening of the individual interactions due to formation of the FMIDLINE HORIZONTAL ELLIPSISF interaction is absent.",
journal = "CrystEngComm",
title = "On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives",
pages = "2622-2606",
number = "13",
volume = "23",
doi = "10.1039/d0ce01841d"
}

Gak Simić, K., Đorđević, I., Lazić, A., Radovanović, L., Petković-Benazzouz, M., Rogan, J., Trišović, N.,& Janjić, G.. (2021). On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives. in CrystEngComm, 23(13), 2606-2622.
https://doi.org/10.1039/d0ce01841d

Gak Simić K, Đorđević I, Lazić A, Radovanović L, Petković-Benazzouz M, Rogan J, Trišović N, Janjić G. On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives. in CrystEngComm. 2021;23(13):2606-2622.
doi:10.1039/d0ce01841d .

Gak Simić, Kristina, Đorđević, Ivana, Lazić, Anita, Radovanović, Lidija, Petković-Benazzouz, Marija, Rogan, Jelena, Trišović, Nemanja, Janjić, Goran, "On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives" in CrystEngComm, 23, no. 13 (2021):2606-2622,
https://doi.org/10.1039/d0ce01841d . .

TY  - JOUR
AU  - Petkovic-Benazzouz, Marija M.
AU  - Rakic, Aleksandra A.
AU  - Trišović, Nemanja
AU  - Zaric, Bozidarka L.
AU  - Janjic, Goran
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4835
AB  - Coordination effects have been considered through the most common interactions in the crystal structures of fluoro compounds (C-H/F and F/F interactions). The supramolecular profile of these effects is based on quantum-chemical calculations for the assessment of the interaction strength and electrostatic potential maps, which provide a qualitative insight into the examined effect. Coordination of aliphatic fluorides leads to an increase of the negative potential of the F atoms, and, hence, an increase in the hydrogen-bonding acceptor ability (strengthening of C-H/F interactions) and a weakening of the F/F interactions, due to an increase in repulsive interactions between the F atoms. There is no significant change in the potential of the F atoms due to coordination of C-6-aromatic fluorides, as in the case of aliphatic ones. This results in slight changes in the strengths of the C-H/F and F/F interactions (coupled with parallel interaction at large offsets, PILO), in a noticeable enhancement of stacking interactions, as well as in a significant enhancement of interactions involving the pi-system (F/pi - and C-H/pi interactions). It has also been shown that a decrease in the charge of the metal ions leads to a decrease in the negative potential of the F atom and also that the nature of the metal ion has a significant influence on the value of the potential of the F atoms.
T2  - Crystal Growth & Design
T1  - Supramolecular Perspective of Coordination Effects on Fluorine Interactions
EP  - 6142
IS  - 11
SP  - 6129
VL  - 21
DO  - 10.1021/acs.cgd.1c00584
ER  - 

@article{
author = "Petkovic-Benazzouz, Marija M. and Rakic, Aleksandra A. and Trišović, Nemanja and Zaric, Bozidarka L. and Janjic, Goran",
year = "2021",
abstract = "Coordination effects have been considered through the most common interactions in the crystal structures of fluoro compounds (C-H/F and F/F interactions). The supramolecular profile of these effects is based on quantum-chemical calculations for the assessment of the interaction strength and electrostatic potential maps, which provide a qualitative insight into the examined effect. Coordination of aliphatic fluorides leads to an increase of the negative potential of the F atoms, and, hence, an increase in the hydrogen-bonding acceptor ability (strengthening of C-H/F interactions) and a weakening of the F/F interactions, due to an increase in repulsive interactions between the F atoms. There is no significant change in the potential of the F atoms due to coordination of C-6-aromatic fluorides, as in the case of aliphatic ones. This results in slight changes in the strengths of the C-H/F and F/F interactions (coupled with parallel interaction at large offsets, PILO), in a noticeable enhancement of stacking interactions, as well as in a significant enhancement of interactions involving the pi-system (F/pi - and C-H/pi interactions). It has also been shown that a decrease in the charge of the metal ions leads to a decrease in the negative potential of the F atom and also that the nature of the metal ion has a significant influence on the value of the potential of the F atoms.",
journal = "Crystal Growth & Design",
title = "Supramolecular Perspective of Coordination Effects on Fluorine Interactions",
pages = "6142-6129",
number = "11",
volume = "21",
doi = "10.1021/acs.cgd.1c00584"
}

Petkovic-Benazzouz, M. M., Rakic, A. A., Trišović, N., Zaric, B. L.,& Janjic, G.. (2021). Supramolecular Perspective of Coordination Effects on Fluorine Interactions. in Crystal Growth & Design, 21(11), 6129-6142.
https://doi.org/10.1021/acs.cgd.1c00584

Petkovic-Benazzouz MM, Rakic AA, Trišović N, Zaric BL, Janjic G. Supramolecular Perspective of Coordination Effects on Fluorine Interactions. in Crystal Growth & Design. 2021;21(11):6129-6142.
doi:10.1021/acs.cgd.1c00584 .

Petkovic-Benazzouz, Marija M., Rakic, Aleksandra A., Trišović, Nemanja, Zaric, Bozidarka L., Janjic, Goran, "Supramolecular Perspective of Coordination Effects on Fluorine Interactions" in Crystal Growth & Design, 21, no. 11 (2021):6129-6142,
https://doi.org/10.1021/acs.cgd.1c00584 . .