Aggregation feature of fluorine-substituted benzene rings and intermolecular C-H.F interaction: crystal structure analyses of mono- and trifluoro-L-phenylalanines |
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Authors: | In Yasuko Kishima Shouitirou Minoura Katsuhiko Nose Takeru Shimohigashi Yasuyuki Ishida Toshimasa |
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Institution: | Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences, Osaka, Japan. in@gly.oups.ac.jp |
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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. |
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