Matrix-isolation FT-IR and theoretical investigation of the competitive intramolecular hydrogen bonding in 5-methyl-3-nitro-2-hydroxyacetophenone |
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Authors: | J. Pajak G. Maes W.M. De Borggraeve N. Boens A. Filarowski |
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Affiliation: | aFaculty of Chemistry, University of Wroclaw, Joliot-Curie 14, 50-383 Wroclaw, Poland;bDepartment of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f – bus 02404 3001 Leuven, Belgium |
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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…ON has been found to be more stable than the conformation with the OH…OC 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. |
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Keywords: | Ortho-hydroxyacetophenone Intramolecular H-bonding Matrix-isolation FT-IR spectroscopy DFT calculations |
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