Hydrogen bonding interactions of α-phenylcinnamic acid isomers in the liquid phase studied by IR and NMR spectroscopies and computational methods

I. Pálinkó, B. Török, M. Rózsa-Tarjányi, J. T. Kiss, G. Tasi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Intra- and intermolecular hydrogen bonding interactions of α-phenylcinnamic acid isomers were studied in the solution phase by infrared (IR) and proton nuclear magnetic resonance ( lH NMR) spectroscopies and the AM1 semi-empirical method. The solvents were CDCl 3 or dimethyl sulfoxide (DMSO), the concentration of the acid isomers were varied. Spectroscopic measurements revealed that (i) intermolecular hydrogen bonds are typical for both acid isomers via their carboxylic groups (OH...0 hydrogen bonding), monomer acids were only present in significant amounts at l0 -4 mol/dm 3 and (ii) CDCl 3 was not involved in the aggregated structures of any isomers, while the oxygen in DMSO seemed to interact with the olefinic proton of the E isomer. Weak intramolecular hydrogen bonds could be identified computationally in the 2 isomer: (aromatic)C-H...O, C = O...H, but none in the E.

Original languageEnglish
Pages (from-to)57-60
Number of pages4
JournalJournal of Molecular Structure
Volume348
DOIs
Publication statusPublished - Mar 15 1995

Fingerprint

Computational methods
Isomers
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Hydrogen bonds
Acids
Liquids
Dimethyl Sulfoxide
Nuclear magnetic resonance
Magnetic resonance spectroscopy
Protons
Monomers
Oxygen
Infrared radiation

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Hydrogen bonding interactions of α-phenylcinnamic acid isomers in the liquid phase studied by IR and NMR spectroscopies and computational methods. / Pálinkó, I.; Török, B.; Rózsa-Tarjányi, M.; Kiss, J. T.; Tasi, G.

In: Journal of Molecular Structure, Vol. 348, 15.03.1995, p. 57-60.

Research output: Contribution to journalArticle

@article{0051b6423d0a41be840678b82cbd438f,
title = "Hydrogen bonding interactions of α-phenylcinnamic acid isomers in the liquid phase studied by IR and NMR spectroscopies and computational methods",
abstract = "Intra- and intermolecular hydrogen bonding interactions of α-phenylcinnamic acid isomers were studied in the solution phase by infrared (IR) and proton nuclear magnetic resonance ( lH NMR) spectroscopies and the AM1 semi-empirical method. The solvents were CDCl 3 or dimethyl sulfoxide (DMSO), the concentration of the acid isomers were varied. Spectroscopic measurements revealed that (i) intermolecular hydrogen bonds are typical for both acid isomers via their carboxylic groups (OH...0 hydrogen bonding), monomer acids were only present in significant amounts at l0 -4 mol/dm 3 and (ii) CDCl 3 was not involved in the aggregated structures of any isomers, while the oxygen in DMSO seemed to interact with the olefinic proton of the E isomer. Weak intramolecular hydrogen bonds could be identified computationally in the 2 isomer: (aromatic)C-H...O, C = O...H, but none in the E.",
author = "I. P{\'a}link{\'o} and B. T{\"o}r{\"o}k and M. R{\'o}zsa-Tarj{\'a}nyi and Kiss, {J. T.} and G. Tasi",
year = "1995",
month = "3",
day = "15",
doi = "10.1016/0022-2860(95)08588-M",
language = "English",
volume = "348",
pages = "57--60",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",

}

TY - JOUR

T1 - Hydrogen bonding interactions of α-phenylcinnamic acid isomers in the liquid phase studied by IR and NMR spectroscopies and computational methods

AU - Pálinkó, I.

AU - Török, B.

AU - Rózsa-Tarjányi, M.

AU - Kiss, J. T.

AU - Tasi, G.

PY - 1995/3/15

Y1 - 1995/3/15

N2 - Intra- and intermolecular hydrogen bonding interactions of α-phenylcinnamic acid isomers were studied in the solution phase by infrared (IR) and proton nuclear magnetic resonance ( lH NMR) spectroscopies and the AM1 semi-empirical method. The solvents were CDCl 3 or dimethyl sulfoxide (DMSO), the concentration of the acid isomers were varied. Spectroscopic measurements revealed that (i) intermolecular hydrogen bonds are typical for both acid isomers via their carboxylic groups (OH...0 hydrogen bonding), monomer acids were only present in significant amounts at l0 -4 mol/dm 3 and (ii) CDCl 3 was not involved in the aggregated structures of any isomers, while the oxygen in DMSO seemed to interact with the olefinic proton of the E isomer. Weak intramolecular hydrogen bonds could be identified computationally in the 2 isomer: (aromatic)C-H...O, C = O...H, but none in the E.

AB - Intra- and intermolecular hydrogen bonding interactions of α-phenylcinnamic acid isomers were studied in the solution phase by infrared (IR) and proton nuclear magnetic resonance ( lH NMR) spectroscopies and the AM1 semi-empirical method. The solvents were CDCl 3 or dimethyl sulfoxide (DMSO), the concentration of the acid isomers were varied. Spectroscopic measurements revealed that (i) intermolecular hydrogen bonds are typical for both acid isomers via their carboxylic groups (OH...0 hydrogen bonding), monomer acids were only present in significant amounts at l0 -4 mol/dm 3 and (ii) CDCl 3 was not involved in the aggregated structures of any isomers, while the oxygen in DMSO seemed to interact with the olefinic proton of the E isomer. Weak intramolecular hydrogen bonds could be identified computationally in the 2 isomer: (aromatic)C-H...O, C = O...H, but none in the E.

UR - http://www.scopus.com/inward/record.url?scp=0002031429&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0002031429&partnerID=8YFLogxK

U2 - 10.1016/0022-2860(95)08588-M

DO - 10.1016/0022-2860(95)08588-M

M3 - Article

AN - SCOPUS:0002031429

VL - 348

SP - 57

EP - 60

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

ER -