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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

Authors :
Shouitirou Kishima
Takeru Nose
Katsuhiko Minoura
Yasuko In
Toshimasa Ishida
Yasuyuki Shimohigashi
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.

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