Hydrogen bonded networks of methoxy-substituted α-phenylcinnamic acids studied by spectroscopic and computational methods

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Abstract

Measurements by infrared (FT-IR) spectroscopy revealed that in solutions of low concentration the major structure forming force (short-range ordering) between methoxy-substituted α-phenylcinnamic acid stereoisomers was the C=O···H-O intermolecular hydrogen bonding between the carboxylic groups. Under 10-3 mol/dm3 concentration no other secondary intermolecular interaction was found. In solid state, using IR spectroscopy, FT-IR and 13C NMR spectroscopies, it was possible to detect (aromatic)C-H···O hydrogen bonds, which were thought to be responsible for long-range ordering. Through the comparison of 13C chemical shifts in the liquid phase and the solid state (olefinic)C-H···O interactions were sought for. Such interactions could not be found for the methoxy derivatives. Molecular modeling provided structural semiquantitative information for the hydrogen bonds detected by IR spectroscopy and gave additional proof for the existence of (aromatic)C-H···O and the non-existence of (olefinic)C-H···O hydrogen bonds.

Original languageEnglish
Pages (from-to)463-468
Number of pages6
JournalJournal of Molecular Structure
Volume565-566
DOIs
Publication statusPublished - May 30 2001

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Computational methods
Hydrogen
Infrared spectroscopy
Spectrum Analysis
Hydrogen bonds
acids
Acids
hydrogen
hydrogen bonds
spectroscopy
Stereoisomerism
Hydrogen Bonding
solid state
Molecular modeling
Chemical shift
interactions
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance spectroscopy
chemical equilibrium
low concentrations

Keywords

  • E- and Z-2-phenyl-3(2′-methoxyphenyl)propenoic acids and E- and Z-2(2′-methoxyphenyl)-3-phenylpropenoic acids
  • FT-IR and C NMR spectroscopies
  • Hydrogen bonding
  • Molecular modeling

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

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title = "Hydrogen bonded networks of methoxy-substituted α-phenylcinnamic acids studied by spectroscopic and computational methods",
abstract = "Measurements by infrared (FT-IR) spectroscopy revealed that in solutions of low concentration the major structure forming force (short-range ordering) between methoxy-substituted α-phenylcinnamic acid stereoisomers was the C=O···H-O intermolecular hydrogen bonding between the carboxylic groups. Under 10-3 mol/dm3 concentration no other secondary intermolecular interaction was found. In solid state, using IR spectroscopy, FT-IR and 13C NMR spectroscopies, it was possible to detect (aromatic)C-H···O hydrogen bonds, which were thought to be responsible for long-range ordering. Through the comparison of 13C chemical shifts in the liquid phase and the solid state (olefinic)C-H···O interactions were sought for. Such interactions could not be found for the methoxy derivatives. Molecular modeling provided structural semiquantitative information for the hydrogen bonds detected by IR spectroscopy and gave additional proof for the existence of (aromatic)C-H···O and the non-existence of (olefinic)C-H···O hydrogen bonds.",
keywords = "E- and Z-2-phenyl-3(2′-methoxyphenyl)propenoic acids and E- and Z-2(2′-methoxyphenyl)-3-phenylpropenoic acids, FT-IR and C NMR spectroscopies, Hydrogen bonding, Molecular modeling",
author = "Kiss, {J. T.} and K. Felf{\"o}ldi and I. Hannus and I. P{\'a}link{\'o}",
year = "2001",
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T1 - Hydrogen bonded networks of methoxy-substituted α-phenylcinnamic acids studied by spectroscopic and computational methods

AU - Kiss, J. T.

AU - Felföldi, K.

AU - Hannus, I.

AU - Pálinkó, I.

PY - 2001/5/30

Y1 - 2001/5/30

N2 - Measurements by infrared (FT-IR) spectroscopy revealed that in solutions of low concentration the major structure forming force (short-range ordering) between methoxy-substituted α-phenylcinnamic acid stereoisomers was the C=O···H-O intermolecular hydrogen bonding between the carboxylic groups. Under 10-3 mol/dm3 concentration no other secondary intermolecular interaction was found. In solid state, using IR spectroscopy, FT-IR and 13C NMR spectroscopies, it was possible to detect (aromatic)C-H···O hydrogen bonds, which were thought to be responsible for long-range ordering. Through the comparison of 13C chemical shifts in the liquid phase and the solid state (olefinic)C-H···O interactions were sought for. Such interactions could not be found for the methoxy derivatives. Molecular modeling provided structural semiquantitative information for the hydrogen bonds detected by IR spectroscopy and gave additional proof for the existence of (aromatic)C-H···O and the non-existence of (olefinic)C-H···O hydrogen bonds.

AB - Measurements by infrared (FT-IR) spectroscopy revealed that in solutions of low concentration the major structure forming force (short-range ordering) between methoxy-substituted α-phenylcinnamic acid stereoisomers was the C=O···H-O intermolecular hydrogen bonding between the carboxylic groups. Under 10-3 mol/dm3 concentration no other secondary intermolecular interaction was found. In solid state, using IR spectroscopy, FT-IR and 13C NMR spectroscopies, it was possible to detect (aromatic)C-H···O hydrogen bonds, which were thought to be responsible for long-range ordering. Through the comparison of 13C chemical shifts in the liquid phase and the solid state (olefinic)C-H···O interactions were sought for. Such interactions could not be found for the methoxy derivatives. Molecular modeling provided structural semiquantitative information for the hydrogen bonds detected by IR spectroscopy and gave additional proof for the existence of (aromatic)C-H···O and the non-existence of (olefinic)C-H···O hydrogen bonds.

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KW - FT-IR and C NMR spectroscopies

KW - Hydrogen bonding

KW - Molecular modeling

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