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New insight into the photochromic mechanism of 1,3‐diphenyl‐4‐(4‐fluoro)benzal‐5‐pyrazolone N (4)‐phenyl semicarbazone
Author(s) -
Yang Yinling,
Wu Dongling,
Jia Dianzeng,
Liu Lang,
Liu Anjie
Publication year - 2011
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.22457
Subject(s) - photochromism , pyrazolone , chemistry , polarizable continuum model , density functional theory , computational chemistry , semicarbazone , reaction mechanism , polarizability , solvent , solvent effects , photochemistry , medicinal chemistry , organic chemistry , molecule , catalysis
Density functional theory (DFT) calculation has been carried out to investigate the photochromic mechanism of 1, 3‐diphenyl‐4‐(4‐fluoro)benzal‐5‐pyrazolone N (4)‐phenyl semicarbazone. The novel mechanism, proposed by us, has different reaction pathway between the forward and the reverse process. The energy barrier of the forward direction was calculated to be significantly larger than that of the reverse direction (30.35 kcal/mol to 9.88 kcal/mol), which confirms the experimental observation that the forward process needs irradiation of light while the reverse one will take place easily when heated. The solvent effect on the relative stabilities of those isomers that may involve in the reaction has also been investigated by applying the polarizable continuum model (PCM) of the self‐consistent reaction field theory. © 2010 Wiley Periodicals, Inc. Int J Quantum Chem, 2011