Calculated vs. measured IR characteristics of α-phenylcinnamic acid stereoisomers - Structural consequences

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Abstract

Trimerisation of E- and Z-α-phenylcinnamic acid was investigated by semiempirical quantum Chemical methods (AMI and PM3). Full geometry optimisation and the calculation of hydrogen bond parameters (bond length, bond energies) were performed for cyclic and catemer trimers. Formation of cyclic trimer proved to be more favoured for the E isomer, while the proportion of the catemer and cyclic forms was comparable in the case of the Z isomer. IR spectra of both isomers were simulated and found to show the spectral features of the measured ones.

Original languageEnglish
Pages (from-to)463-467
Number of pages5
JournalJournal of Molecular Structure
Volume482-483
DOIs
Publication statusPublished - May 25 1999

Fingerprint

Stereoisomerism
Isomers
Hydrogen
isomers
trimers
acids
Acids
Chemical bonds
Bond length
proportion
Hydrogen bonds
hydrogen bonds
optimization
Geometry
geometry
energy

Keywords

  • α-Phenylcinnamic acid stereoisomers
  • Hydrogen bonds
  • Semiempirical methods
  • Simulation of IR spectra
  • Trimerisation

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 = "Calculated vs. measured IR characteristics of α-phenylcinnamic acid stereoisomers - Structural consequences",
abstract = "Trimerisation of E- and Z-α-phenylcinnamic acid was investigated by semiempirical quantum Chemical methods (AMI and PM3). Full geometry optimisation and the calculation of hydrogen bond parameters (bond length, bond energies) were performed for cyclic and catemer trimers. Formation of cyclic trimer proved to be more favoured for the E isomer, while the proportion of the catemer and cyclic forms was comparable in the case of the Z isomer. IR spectra of both isomers were simulated and found to show the spectral features of the measured ones.",
keywords = "α-Phenylcinnamic acid stereoisomers, Hydrogen bonds, Semiempirical methods, Simulation of IR spectra, Trimerisation",
author = "{\'A}. Kukovecz and I. P{\'a}link{\'o}",
year = "1999",
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doi = "10.1016/S0022-2860(98)00936-3",
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journal = "Journal of Molecular Structure",
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T1 - Calculated vs. measured IR characteristics of α-phenylcinnamic acid stereoisomers - Structural consequences

AU - Kukovecz, Á.

AU - Pálinkó, I.

PY - 1999/5/25

Y1 - 1999/5/25

N2 - Trimerisation of E- and Z-α-phenylcinnamic acid was investigated by semiempirical quantum Chemical methods (AMI and PM3). Full geometry optimisation and the calculation of hydrogen bond parameters (bond length, bond energies) were performed for cyclic and catemer trimers. Formation of cyclic trimer proved to be more favoured for the E isomer, while the proportion of the catemer and cyclic forms was comparable in the case of the Z isomer. IR spectra of both isomers were simulated and found to show the spectral features of the measured ones.

AB - Trimerisation of E- and Z-α-phenylcinnamic acid was investigated by semiempirical quantum Chemical methods (AMI and PM3). Full geometry optimisation and the calculation of hydrogen bond parameters (bond length, bond energies) were performed for cyclic and catemer trimers. Formation of cyclic trimer proved to be more favoured for the E isomer, while the proportion of the catemer and cyclic forms was comparable in the case of the Z isomer. IR spectra of both isomers were simulated and found to show the spectral features of the measured ones.

KW - α-Phenylcinnamic acid stereoisomers

KW - Hydrogen bonds

KW - Semiempirical methods

KW - Simulation of IR spectra

KW - Trimerisation

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