CH⋯S hydrogen bonds as the organising force in 2,3-thienyl- and phenyl- or 2,3-dithienyl-substituted propenoic acid aggregates studied by the combination of FT-IR spectroscopy and computations

K. Csankó, L. Illés, K. Felföldi, J. T. Kiss, P. Sipos, I. Pálinkó

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Various propenoic acid stereoisomers 2,3-disubstituted with thienyl and/or phenyl groups were synthesised and their aggregation behaviour was studied both in solution and in the solid state by experimental (mid-range FT-IR spectroscopy) and computational (semiempirical and ab initio) methods. Experimental approach embraced the identification of potential hydrogen bonding sites through finding the relevant IR bands and monitoring their displacement upon increasing the acid concentration in solution and on going from solution to the solid state. In solution OH⋯O hydrogen bonds were only found providing short-range ordering, while in the solid state CH⋯S hydrogen bonds were identified. 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.

Original languageEnglish
Pages (from-to)259-263
Number of pages5
JournalJournal of Molecular Structure
Volume993
Issue number1-3
DOIs
Publication statusPublished - May 3 2011

Fingerprint

Infrared spectroscopy
Hydrogen bonds
Acids
Stereoisomerism
Molecular modeling
Bond length
Agglomeration
Visualization
Monitoring

Keywords

  • CH⋯S hydrogen bonds
  • Hydrogen bonded network
  • IR spectroscopy
  • Molecular modelling
  • Thienyl and/or phenyl 2,3-disubstituted propenoic acids

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

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title = "CH⋯S hydrogen bonds as the organising force in 2,3-thienyl- and phenyl- or 2,3-dithienyl-substituted propenoic acid aggregates studied by the combination of FT-IR spectroscopy and computations",
abstract = "Various propenoic acid stereoisomers 2,3-disubstituted with thienyl and/or phenyl groups were synthesised and their aggregation behaviour was studied both in solution and in the solid state by experimental (mid-range FT-IR spectroscopy) and computational (semiempirical and ab initio) methods. Experimental approach embraced the identification of potential hydrogen bonding sites through finding the relevant IR bands and monitoring their displacement upon increasing the acid concentration in solution and on going from solution to the solid state. In solution OH⋯O hydrogen bonds were only found providing short-range ordering, while in the solid state CH⋯S hydrogen bonds were identified. 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.",
keywords = "CH⋯S hydrogen bonds, Hydrogen bonded network, IR spectroscopy, Molecular modelling, Thienyl and/or phenyl 2,3-disubstituted propenoic acids",
author = "K. Csank{\'o} and L. Ill{\'e}s and K. Felf{\"o}ldi and Kiss, {J. T.} and P. Sipos and I. P{\'a}link{\'o}",
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journal = "Journal of Molecular Structure",
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T1 - CH⋯S hydrogen bonds as the organising force in 2,3-thienyl- and phenyl- or 2,3-dithienyl-substituted propenoic acid aggregates studied by the combination of FT-IR spectroscopy and computations

AU - Csankó, K.

AU - Illés, L.

AU - Felföldi, K.

AU - Kiss, J. T.

AU - Sipos, P.

AU - Pálinkó, I.

PY - 2011/5/3

Y1 - 2011/5/3

N2 - Various propenoic acid stereoisomers 2,3-disubstituted with thienyl and/or phenyl groups were synthesised and their aggregation behaviour was studied both in solution and in the solid state by experimental (mid-range FT-IR spectroscopy) and computational (semiempirical and ab initio) methods. Experimental approach embraced the identification of potential hydrogen bonding sites through finding the relevant IR bands and monitoring their displacement upon increasing the acid concentration in solution and on going from solution to the solid state. In solution OH⋯O hydrogen bonds were only found providing short-range ordering, while in the solid state CH⋯S hydrogen bonds were identified. 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.

AB - Various propenoic acid stereoisomers 2,3-disubstituted with thienyl and/or phenyl groups were synthesised and their aggregation behaviour was studied both in solution and in the solid state by experimental (mid-range FT-IR spectroscopy) and computational (semiempirical and ab initio) methods. Experimental approach embraced the identification of potential hydrogen bonding sites through finding the relevant IR bands and monitoring their displacement upon increasing the acid concentration in solution and on going from solution to the solid state. In solution OH⋯O hydrogen bonds were only found providing short-range ordering, while in the solid state CH⋯S hydrogen bonds were identified. 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.

KW - CH⋯S hydrogen bonds

KW - Hydrogen bonded network

KW - IR spectroscopy

KW - Molecular modelling

KW - Thienyl and/or phenyl 2,3-disubstituted propenoic acids

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U2 - 10.1016/j.molstruc.2010.09.033

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JF - Journal of Molecular Structure

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