Intramolecular hydrogen bonding in α-phenylcinnamic acids and their heteroatom-containing derivatives studied by ab initio quantum chemical methods

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Abstract

Intramolecular hydrogen bonding interactions were searched for in conformers of isolated α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers. The conformers were obtained by ab initio (HF/3-21G//HF/3-21G and HF/6-31G(d,p)//HF/6-31G(d,p)) quantum chemical methods using initial geometries corresponding to the global minima determined at the level of semi-empirical quantum chemical calculations. The most common intramolecular hydrogen bond was of C-H...O type. In certain conformers of α-(2-pyridyl)cinnamic acids, O-H...Npyridyl and α-(2-furyl)cinnamic acids, O-H...Ofuryl interactions were also found. In most cases, at the level of HF/3-21G calculations, these conformers were more stable than those lacking these close contacts. When the larger basis set was applied the extra stabilizing effect disappeared, nevertheless, these geometries still represented minimum structures.

Original languageEnglish
Pages (from-to)139-149
Number of pages11
JournalJournal of Molecular Structure: THEOCHEM
Volume535
DOIs
Publication statusPublished - Jan 15 2001

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Hydrogen Bonding
Hydrogen bonds
Derivatives
acids
Stereoisomerism
Acids
Geometry
hydrogen
Hydrogen
geometry
interactions
hydrogen bonds
cinnamic acid

Keywords

  • α-phenyl-
  • α-pyridyl- and α-furylcinnamic acid stereoisomers
  • Ab initio (HF/3-21G and HF/6-31G(d,p)) calculations
  • Geometric cut-off criteria
  • Intramolecular hydrogen bonding

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

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title = "Intramolecular hydrogen bonding in α-phenylcinnamic acids and their heteroatom-containing derivatives studied by ab initio quantum chemical methods",
abstract = "Intramolecular hydrogen bonding interactions were searched for in conformers of isolated α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers. The conformers were obtained by ab initio (HF/3-21G//HF/3-21G and HF/6-31G(d,p)//HF/6-31G(d,p)) quantum chemical methods using initial geometries corresponding to the global minima determined at the level of semi-empirical quantum chemical calculations. The most common intramolecular hydrogen bond was of C-H...O type. In certain conformers of α-(2-pyridyl)cinnamic acids, O-H...Npyridyl and α-(2-furyl)cinnamic acids, O-H...Ofuryl interactions were also found. In most cases, at the level of HF/3-21G calculations, these conformers were more stable than those lacking these close contacts. When the larger basis set was applied the extra stabilizing effect disappeared, nevertheless, these geometries still represented minimum structures.",
keywords = "α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers, Ab initio (HF/3-21G and HF/6-31G(d,p)) calculations, Geometric cut-off criteria, Intramolecular hydrogen bonding",
author = "T. K{\"o}rtv{\'e}lyesi and {\'A}. Kukovecz and S. Lovas and I. P{\'a}link{\'o}",
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T1 - Intramolecular hydrogen bonding in α-phenylcinnamic acids and their heteroatom-containing derivatives studied by ab initio quantum chemical methods

AU - Körtvélyesi, T.

AU - Kukovecz, Á.

AU - Lovas, S.

AU - Pálinkó, I.

PY - 2001/1/15

Y1 - 2001/1/15

N2 - Intramolecular hydrogen bonding interactions were searched for in conformers of isolated α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers. The conformers were obtained by ab initio (HF/3-21G//HF/3-21G and HF/6-31G(d,p)//HF/6-31G(d,p)) quantum chemical methods using initial geometries corresponding to the global minima determined at the level of semi-empirical quantum chemical calculations. The most common intramolecular hydrogen bond was of C-H...O type. In certain conformers of α-(2-pyridyl)cinnamic acids, O-H...Npyridyl and α-(2-furyl)cinnamic acids, O-H...Ofuryl interactions were also found. In most cases, at the level of HF/3-21G calculations, these conformers were more stable than those lacking these close contacts. When the larger basis set was applied the extra stabilizing effect disappeared, nevertheless, these geometries still represented minimum structures.

AB - Intramolecular hydrogen bonding interactions were searched for in conformers of isolated α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers. The conformers were obtained by ab initio (HF/3-21G//HF/3-21G and HF/6-31G(d,p)//HF/6-31G(d,p)) quantum chemical methods using initial geometries corresponding to the global minima determined at the level of semi-empirical quantum chemical calculations. The most common intramolecular hydrogen bond was of C-H...O type. In certain conformers of α-(2-pyridyl)cinnamic acids, O-H...Npyridyl and α-(2-furyl)cinnamic acids, O-H...Ofuryl interactions were also found. In most cases, at the level of HF/3-21G calculations, these conformers were more stable than those lacking these close contacts. When the larger basis set was applied the extra stabilizing effect disappeared, nevertheless, these geometries still represented minimum structures.

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KW - Geometric cut-off criteria

KW - Intramolecular hydrogen bonding

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