Journal of Molecular Structure vol:880 issue:1-3 pages:86-96
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 center dot center dot center dot O=N has been found to be more stable than the conformation with the OH center dot center dot center dot O=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. (c) 2007 Elsevier B.V. All rights reserved.