C{single bond}H...F hydrogen bonds as the organising force in F-substituted α-phenyl cinnamic acid aggregates studied by the combination of FTIR spectroscopy and computations

B. Tolnai, J. T. Kiss, K. Felföldi, I. Pálinkó

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Various F-substituted E-2,3-diphenyl propenoic acid molecules were synthesised and their aggregation behaviour was studied by experimental (FT-IR spectroscopy) and computational (semiempirical and DFT) methods. Experimental approach embraced the identification of potential hydrogen bonding sites through finding the relevant IR bands and monitoring their shifts upon increasing the acid concentration and on going to the solid state. It was found that fluorine engaged in C{single bond}H...F hydrogen bonding easily, where the carbon atom could be of any kind available in the molecule (aromatic, aliphatic or olefinic). Shifts were found even in moderately concentrated solutions and in the solid state too. Hydrogen bonding sites could be assigned and relevant aggregate models could be built. Molecular modelling allowed obtaining good estimates for hydrogen bond lengths and angles and visualisation of the geometric arrangements even of extended networks also became feasible.

Original languageEnglish
Pages (from-to)27-31
Number of pages5
JournalJournal of Molecular Structure
Volume924-926
Issue numberC
DOIs
Publication statusPublished - Apr 30 2009

Keywords

  • C{single bond}H...F hydrogen bonds
  • F-substituted E-2,3-diphenyl propenoic acid
  • Hydrogen-bonded network
  • IR spectroscopy
  • Molecular modelling

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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