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Aggregation Feature of Fluorine-Substituted Benzene Rings and Intermolecular C-H...F Interaction: Crystal Structure Analyses of Mono- and Trifluoro-L-phenylalanines
Aggregation Feature of Fluorine-Substituted Benzene Rings and Intermolecular C-H...F Interaction: Crystal Structure Analyses of Mono- and Trifluoro-L-phenylalanines
- Source :
- Chemical and Pharmaceutical Bulletin. 51:1258-1263
- Publication Year :
- 2003
- Publisher :
- Pharmaceutical Society of Japan, 2003.
-
Abstract
- X-Ray crystal structures of four different fluorine-substituted phenylalanines (two mono- and two tri-substitutions) were analyzed to investigate the effect of fluorine atom on the association pattern of benzene rings. Although respective structures showed similar molecular packing in such a way that the layers of hydrophobic benzene rings and hydrophilic amino/carboxyl groups were alternately running along a crystallographic axis, the association patterns of benzene rings were different depending on the substitution position and number of fluorine atoms. The general features could be that the partially displaced face-to-face interactions are increased with increase in the number of fluorine atoms, whereas the edge-to-face interactions are decreased. The C-H bond next to a fluorine-substituted carbon atom could serve as a donor of an intermolecular C-H.F hydrogen bond.
- Subjects :
- Models, Molecular
Chemical Phenomena
Stereochemistry
Phenylalanine
Molecular Conformation
chemistry.chemical_element
Crystal structure
Crystallography, X-Ray
law.invention
chemistry.chemical_compound
law
Drug Discovery
Molecule
Crystallization
Benzene
Chemistry, Physical
Chemistry
Hydrogen bond
Intermolecular force
X-ray
Hydrogen Bonding
General Chemistry
General Medicine
Fluorobenzenes
Crystallography
Fluorine
Receptors, Thrombin
Subjects
Details
- ISSN :
- 13475223 and 00092363
- Volume :
- 51
- Database :
- OpenAIRE
- Journal :
- Chemical and Pharmaceutical Bulletin
- Accession number :
- edsair.doi.dedup.....ab06582eeabdaba3c932a169a3bcf284
- Full Text :
- https://doi.org/10.1248/cpb.51.1258