Structural features of pyridylcinnamic acid dimers and their extended hydrogen-bonded aggregations

K. Csankó, K. I. Ruusuvuori, B. Tolnai, P. Sipos, O. Berkesi, I. Pálinkó

Research output: Contribution to journalArticle

Abstract

The conformational as well as the structure-forming properties of E-3-(x-pyridyl)propenoic acids (x = 2, 3 or 4) have been studied with a combination of computational and spectroscopic methods. IR spectroscopy revealed that in the solid state the zwitterionic species predominate, while NMR measurements showed that dimers, kept together by strong CO⋯HO hydrogen bonds, were formed in a dipolar aprotic solvent (DMSO). In concentrated solution, extended aggregation occurred through the cooperative effect of (aromatic) C-H⋯N weak hydrogen bonds. Conformational search was performed at the HF/6-31G(d,p) level of theory. Comparison with experimental values as well as benchmarking calculations at several different levels of theory to probe the performance of the methods, B3LYP/6-31G++(d,p) method was found to be able to provide reasonable geometries as well as quantitative formation energies for the dimers and the tetramers, too.

Original languageEnglish
Pages (from-to)25-33
Number of pages9
JournalJournal of Molecular Structure
Volume1090
DOIs
Publication statusPublished - Jun 15 2015

Fingerprint

Dimers
Hydrogen
Hydrogen bonds
Agglomeration
Acids
Benchmarking
Dimethyl Sulfoxide
Infrared spectroscopy
Nuclear magnetic resonance
Geometry

Keywords

  • Conformational search
  • Modelling intermolecular hydrogen bonds
  • Pyridylpropenoic acids
  • Spectroscopic methods

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Structural features of pyridylcinnamic acid dimers and their extended hydrogen-bonded aggregations. / Csankó, K.; Ruusuvuori, K. I.; Tolnai, B.; Sipos, P.; Berkesi, O.; Pálinkó, I.

In: Journal of Molecular Structure, Vol. 1090, 15.06.2015, p. 25-33.

Research output: Contribution to journalArticle

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AU - Sipos, P.

AU - Berkesi, O.

AU - Pálinkó, I.

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AB - The conformational as well as the structure-forming properties of E-3-(x-pyridyl)propenoic acids (x = 2, 3 or 4) have been studied with a combination of computational and spectroscopic methods. IR spectroscopy revealed that in the solid state the zwitterionic species predominate, while NMR measurements showed that dimers, kept together by strong CO⋯HO hydrogen bonds, were formed in a dipolar aprotic solvent (DMSO). In concentrated solution, extended aggregation occurred through the cooperative effect of (aromatic) C-H⋯N weak hydrogen bonds. Conformational search was performed at the HF/6-31G(d,p) level of theory. Comparison with experimental values as well as benchmarking calculations at several different levels of theory to probe the performance of the methods, B3LYP/6-31G++(d,p) method was found to be able to provide reasonable geometries as well as quantitative formation energies for the dimers and the tetramers, too.

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