Matrix-isolation FT-IR and theoretical investigation of the competitive intramolecular hydrogen bonding in 5-methyl-3-nitro-2-hydroxyacetophenone

J. Pajak, G. Maes, W. M. De Borggraeve, N. Boens, A. Filarowski

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The paper presents the conformational, vibrational and hydrogen bond characteristics of 5-methyl-3-nitro-2-hydroxyacetophenone studied with the combined matrix-isolation FT-IR spectroscopic and theoretical (DFT/B3LYP/6-31++G**) technique. Theoretical calculations predict three stable conformations of the studied compound. Only two of these conformations could be identified experimentally using the matrix-isolation FT-IR technique. The conformation with the intramolecular hydrogen bond OH...O{double bond, long}N has been found to be more stable than the conformation with the OH...O{double bond, long}C type of hydrogen bond by 7.28 kJ/mol. The complete assignment of the experimental spectra could be performed based on the theoretical calculations including the normal coordinate analysis and isotopic substitution.

Original languageEnglish
Pages (from-to)86-96
Number of pages11
JournalJournal of Molecular Structure
Volume880
Issue number1-3
DOIs
Publication statusPublished - May 27 2008
Externally publishedYes

Keywords

  • DFT calculations
  • Intramolecular H-bonding
  • Matrix-isolation FT-IR spectroscopy
  • Ortho-hydroxyacetophenone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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