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  - 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 . .