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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.
- Source :
-
Chemical & pharmaceutical bulletin [Chem Pharm Bull (Tokyo)] 2003 Nov; Vol. 51 (11), pp. 1258-63. - Publication Year :
- 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
- Language :
- English
- ISSN :
- 0009-2363
- Volume :
- 51
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- Chemical & pharmaceutical bulletin
- Publication Type :
- Academic Journal
- Accession number :
- 14600369
- Full Text :
- https://doi.org/10.1248/cpb.51.1258