Modeling hydrogen bonding interactions in α-substituted cinnamic acid ester derivatives by semiempirical quantum chemical calculations

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Intermolecular hydrogen bonding interactions in stereoisomeric α-substituted cinnamic acid methyl esters and their methoxy substituted derivatives were studied by model calculations at the semiempirical quantum chemical level of theory. Intermolecular hydrogen bonds of C-H···O types were found to be general. In this type of interaction the carbon may be part of either aromatic ring, the olefinic bond, the methyl carbon of the methyl ester or the methyl carbon of the methoxy group. The hydrogen bond acceptor may be the carbonyl oxygen or the oxygen in the methoxy substituent. Modeling helped in determining probable hydrogen bonding sites and their positions and provided with approximate geometric parameters (bond lengths and angles). (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)99-103
Number of pages5
JournalJournal of Molecular Structure: THEOCHEM
Volume531
DOIs
Publication statusPublished - Oct 23 2000

Fingerprint

Hydrogen Bonding
esters
Esters
Hydrogen bonds
Carbon
Derivatives
acids
Acids
Hydrogen
carbon
hydrogen
hydrogen bonds
Oxygen
interactions
oxygen
Bond length
rings
cinnamic acid

Keywords

  • Intermolecular hydrogen bonds
  • Semiempirical quantum chemical calculations
  • Stereoisomeric α-substituted cinnamic acid methyl esters

ASJC Scopus subject areas

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

Cite this

@article{1de09145fcf349189eafa83c374bb573,
title = "Modeling hydrogen bonding interactions in α-substituted cinnamic acid ester derivatives by semiempirical quantum chemical calculations",
abstract = "Intermolecular hydrogen bonding interactions in stereoisomeric α-substituted cinnamic acid methyl esters and their methoxy substituted derivatives were studied by model calculations at the semiempirical quantum chemical level of theory. Intermolecular hydrogen bonds of C-H···O types were found to be general. In this type of interaction the carbon may be part of either aromatic ring, the olefinic bond, the methyl carbon of the methyl ester or the methyl carbon of the methoxy group. The hydrogen bond acceptor may be the carbonyl oxygen or the oxygen in the methoxy substituent. Modeling helped in determining probable hydrogen bonding sites and their positions and provided with approximate geometric parameters (bond lengths and angles). (C) 2000 Elsevier Science B.V.",
keywords = "Intermolecular hydrogen bonds, Semiempirical quantum chemical calculations, Stereoisomeric α-substituted cinnamic acid methyl esters",
author = "T. K{\"o}rtv{\'e}lyesi and I. P{\'a}link{\'o}",
year = "2000",
month = "10",
day = "23",
doi = "10.1016/S0166-1280(00)00436-X",
language = "English",
volume = "531",
pages = "99--103",
journal = "Computational and Theoretical Chemistry",
issn = "2210-271X",
publisher = "Elsevier BV",

}

TY - JOUR

T1 - Modeling hydrogen bonding interactions in α-substituted cinnamic acid ester derivatives by semiempirical quantum chemical calculations

AU - Körtvélyesi, T.

AU - Pálinkó, I.

PY - 2000/10/23

Y1 - 2000/10/23

N2 - Intermolecular hydrogen bonding interactions in stereoisomeric α-substituted cinnamic acid methyl esters and their methoxy substituted derivatives were studied by model calculations at the semiempirical quantum chemical level of theory. Intermolecular hydrogen bonds of C-H···O types were found to be general. In this type of interaction the carbon may be part of either aromatic ring, the olefinic bond, the methyl carbon of the methyl ester or the methyl carbon of the methoxy group. The hydrogen bond acceptor may be the carbonyl oxygen or the oxygen in the methoxy substituent. Modeling helped in determining probable hydrogen bonding sites and their positions and provided with approximate geometric parameters (bond lengths and angles). (C) 2000 Elsevier Science B.V.

AB - Intermolecular hydrogen bonding interactions in stereoisomeric α-substituted cinnamic acid methyl esters and their methoxy substituted derivatives were studied by model calculations at the semiempirical quantum chemical level of theory. Intermolecular hydrogen bonds of C-H···O types were found to be general. In this type of interaction the carbon may be part of either aromatic ring, the olefinic bond, the methyl carbon of the methyl ester or the methyl carbon of the methoxy group. The hydrogen bond acceptor may be the carbonyl oxygen or the oxygen in the methoxy substituent. Modeling helped in determining probable hydrogen bonding sites and their positions and provided with approximate geometric parameters (bond lengths and angles). (C) 2000 Elsevier Science B.V.

KW - Intermolecular hydrogen bonds

KW - Semiempirical quantum chemical calculations

KW - Stereoisomeric α-substituted cinnamic acid methyl esters

UR - http://www.scopus.com/inward/record.url?scp=0034706710&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034706710&partnerID=8YFLogxK

U2 - 10.1016/S0166-1280(00)00436-X

DO - 10.1016/S0166-1280(00)00436-X

M3 - Article

AN - SCOPUS:0034706710

VL - 531

SP - 99

EP - 103

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

ER -