Aggregation feature of fluorine-substituted benzene rings and intermolecular C-H⋯f interaction: Crystal structure analyses of mono- and trifluoro-L-phenylalanines

In Yasuko, Shouitirou Kishima, Katsuhiko Minoura, Takeru Nose, Yasuyuki Shimohigashi, Toshimasa Ishida

Research output: Contribution to journalArticle

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1258-1263
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume51
Issue number11
DOIs
Publication statusPublished - Nov 1 2003

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Fluorine
Benzene
Phenylalanine
Agglomeration
Crystal structure
Atoms
Substitution reactions
Association reactions
Hydrogen
Hydrogen bonds
Carbon
X-Rays
X rays

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Aggregation feature of fluorine-substituted benzene rings and intermolecular C-H⋯f interaction : Crystal structure analyses of mono- and trifluoro-L-phenylalanines. / Yasuko, In; Kishima, Shouitirou; Minoura, Katsuhiko; Nose, Takeru; Shimohigashi, Yasuyuki; Ishida, Toshimasa.

In: Chemical and Pharmaceutical Bulletin, Vol. 51, No. 11, 01.11.2003, p. 1258-1263.

Research output: Contribution to journalArticle

Yasuko, In ; Kishima, Shouitirou ; Minoura, Katsuhiko ; Nose, Takeru ; Shimohigashi, Yasuyuki ; Ishida, Toshimasa. / Aggregation feature of fluorine-substituted benzene rings and intermolecular C-H⋯f interaction : Crystal structure analyses of mono- and trifluoro-L-phenylalanines. In: Chemical and Pharmaceutical Bulletin. 2003 ; Vol. 51, No. 11. pp. 1258-1263.
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AU - Ishida, Toshimasa

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