Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 51, Issue 11, Pages 1258-1263Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.51.1258
Keywords
fluorophenylalanine; crystal structure; benzene-benzene interaction; C-H center dot center dot center dot F interaction
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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.
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