Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/18070
Title: Positive Identification of UV-Generated, Non-Hydrogen-Bonded Isomers of o-Hydroxybenzaldehyde and o-Hydroxyacetophenone
Authors: Lapinski, Leszek 
Rostkowska, Hanna 
Reva, Igor 
Fausto, Rui 
Nowak, Maciej J. 
Issue Date: Apr-2010
Publisher: American Chemical Society
Serial title, monograph or event: J. Phys. Chem. A
Volume: 114
Abstract: Non-hydrogen-bonded isomers were photogenerated by UV (λ > 335 nm) irradiation of o-hydroxybenzaldehyde (salicylaldehyde) and o-hydroxyacetophenone monomers isolated in low-temperature Ar matrixes. These photoisomerizations were found to be photoreversible. Upon shorter wavelength (λ > 235 nm or λ > 270 nm) UV irradiation, the initial forms of the compounds (with intramolecular hydrogen bonds) were partially repopulated. The structures of the photogenerated non-hydrogen-bonded isomers of both compounds were positively identified by comparison of their IR spectra with the spectra theoretically calculated [at the DFT(B3LYP)/6-311++G(2d,p) level] for all possible non-hydrogen-bonded isomers of the studied compounds. The experimental IR spectra of the photoproducts generated from o-hydroxybenzaldehyde and o-hydroxyacetophenone are very well reproduced only by the theoretical spectra predicted for the isomers with both OH and formyl (or acetyl) groups rotated by 180°, with respect to the initial, most stable hydrogen-bonded conformer. Excellent agreement between experiment and theoretical prediction provides a basis for a very reliable identification of the photoproduced isomers of o-hydroxybenzaldehyde and o-hydroxyacetophenone.
URI: http://hdl.handle.net/10316/18070
DOI: 10.1021/jp1003775
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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