The application of crystallographic data for study of interactions of fluorine atom in the crystal structure of small molecules
Primena kristalografskih podataka u ispitivanju interakcija fluora u kristalnim strukturama malih molekula
Конференцијски прилог (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Large number of compounds has halogens incorporated in their structure. Halogens
have an anisotropic charge distribution with a region of negative charge and a region of
positive charge along the C-X bond (σ-hole). Larger halogens form more positive σ-hole,
while the size of the σ-hole is affected by the electronegativity of the atoms bonded to halogen
atom. Fluorine behaves different from other halogens, because the character to the C-F bond
depends on the local environment of the fluorine, which might be relevant for the type and
nature of molecular interactions of fluorine atoms. In Protein Data Bank, the fluorine atoms are
found preferentially in close contact with hydrophobic side-chains and in close to carbonyl
group.
The interactions of fluorine atoms were studied by analyzing data from the crystal
structures of small molecules, archived in the Cambridge Structural Database (CSD).
Statistical analysis showed that the most abundant are structures in which F atoms build...
hydrogen bonds. Among them the CH/F interactions are more frequent (68707 interactions)
than classical hydrogen bonds (4703 NH/F and 2882 OH/F interactions). Surprisingly, the
XF/F and XF/O interactions were shown to be abundant in the crystal structures (Figure).
However, the most common interactions of fluorine atom in the CSD are interactions between
two fluorine atoms (150993 XF/F interactions).
The results of quantum-chemical calculations showed that the most stable XF/F
interaction occurs between two CH3F molecules with energy of -1.45 kcal/mol. These
interactions are significantly weaker than classical hydrogen bonds. The large abundance
of XF/F interactions in crystal structures can be explained by tendency of fluorine atoms
to form three or more simultaneous interactions with species from the environment.
Кључне речи:
fluorine, non-covalent interactions, crystallographyИзвор:
22nd CONFERENCE OF THE SERBIAN CRYSTALLOGRAPHIC SOCIETY, 2015Издавач:
- Serbian Crystallographic Society
Институција/група
Institut za multidisciplinarna istraživanjaTY - CONF AU - Janjić, Goran AU - Jelić, Stefan AU - Radibratovic, Milica AU - Milčić, Miloš PY - 2015 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/3061 AB - Large number of compounds has halogens incorporated in their structure. Halogens have an anisotropic charge distribution with a region of negative charge and a region of positive charge along the C-X bond (σ-hole). Larger halogens form more positive σ-hole, while the size of the σ-hole is affected by the electronegativity of the atoms bonded to halogen atom. Fluorine behaves different from other halogens, because the character to the C-F bond depends on the local environment of the fluorine, which might be relevant for the type and nature of molecular interactions of fluorine atoms. In Protein Data Bank, the fluorine atoms are found preferentially in close contact with hydrophobic side-chains and in close to carbonyl group. The interactions of fluorine atoms were studied by analyzing data from the crystal structures of small molecules, archived in the Cambridge Structural Database (CSD). Statistical analysis showed that the most abundant are structures in which F atoms build hydrogen bonds. Among them the CH/F interactions are more frequent (68707 interactions) than classical hydrogen bonds (4703 NH/F and 2882 OH/F interactions). Surprisingly, the XF/F and XF/O interactions were shown to be abundant in the crystal structures (Figure). However, the most common interactions of fluorine atom in the CSD are interactions between two fluorine atoms (150993 XF/F interactions). The results of quantum-chemical calculations showed that the most stable XF/F interaction occurs between two CH3F molecules with energy of -1.45 kcal/mol. These interactions are significantly weaker than classical hydrogen bonds. The large abundance of XF/F interactions in crystal structures can be explained by tendency of fluorine atoms to form three or more simultaneous interactions with species from the environment. PB - Serbian Crystallographic Society C3 - 22nd CONFERENCE OF THE SERBIAN CRYSTALLOGRAPHIC SOCIETY T1 - The application of crystallographic data for study of interactions of fluorine atom in the crystal structure of small molecules T1 - Primena kristalografskih podataka u ispitivanju interakcija fluora u kristalnim strukturama malih molekula UR - https://hdl.handle.net/21.15107/rcub_rimsi_3061 ER -
@conference{ author = "Janjić, Goran and Jelić, Stefan and Radibratovic, Milica and Milčić, Miloš", year = "2015", abstract = "Large number of compounds has halogens incorporated in their structure. Halogens have an anisotropic charge distribution with a region of negative charge and a region of positive charge along the C-X bond (σ-hole). Larger halogens form more positive σ-hole, while the size of the σ-hole is affected by the electronegativity of the atoms bonded to halogen atom. Fluorine behaves different from other halogens, because the character to the C-F bond depends on the local environment of the fluorine, which might be relevant for the type and nature of molecular interactions of fluorine atoms. In Protein Data Bank, the fluorine atoms are found preferentially in close contact with hydrophobic side-chains and in close to carbonyl group. The interactions of fluorine atoms were studied by analyzing data from the crystal structures of small molecules, archived in the Cambridge Structural Database (CSD). Statistical analysis showed that the most abundant are structures in which F atoms build hydrogen bonds. Among them the CH/F interactions are more frequent (68707 interactions) than classical hydrogen bonds (4703 NH/F and 2882 OH/F interactions). Surprisingly, the XF/F and XF/O interactions were shown to be abundant in the crystal structures (Figure). However, the most common interactions of fluorine atom in the CSD are interactions between two fluorine atoms (150993 XF/F interactions). The results of quantum-chemical calculations showed that the most stable XF/F interaction occurs between two CH3F molecules with energy of -1.45 kcal/mol. These interactions are significantly weaker than classical hydrogen bonds. The large abundance of XF/F interactions in crystal structures can be explained by tendency of fluorine atoms to form three or more simultaneous interactions with species from the environment.", publisher = "Serbian Crystallographic Society", journal = "22nd CONFERENCE OF THE SERBIAN CRYSTALLOGRAPHIC SOCIETY", title = "The application of crystallographic data for study of interactions of fluorine atom in the crystal structure of small molecules, Primena kristalografskih podataka u ispitivanju interakcija fluora u kristalnim strukturama malih molekula", url = "https://hdl.handle.net/21.15107/rcub_rimsi_3061" }
Janjić, G., Jelić, S., Radibratovic, M.,& Milčić, M.. (2015). The application of crystallographic data for study of interactions of fluorine atom in the crystal structure of small molecules. in 22nd CONFERENCE OF THE SERBIAN CRYSTALLOGRAPHIC SOCIETY Serbian Crystallographic Society.. https://hdl.handle.net/21.15107/rcub_rimsi_3061
Janjić G, Jelić S, Radibratovic M, Milčić M. The application of crystallographic data for study of interactions of fluorine atom in the crystal structure of small molecules. in 22nd CONFERENCE OF THE SERBIAN CRYSTALLOGRAPHIC SOCIETY. 2015;. https://hdl.handle.net/21.15107/rcub_rimsi_3061 .
Janjić, Goran, Jelić, Stefan, Radibratovic, Milica, Milčić, Miloš, "The application of crystallographic data for study of interactions of fluorine atom in the crystal structure of small molecules" in 22nd CONFERENCE OF THE SERBIAN CRYSTALLOGRAPHIC SOCIETY (2015), https://hdl.handle.net/21.15107/rcub_rimsi_3061 .