Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5419325 | Journal of Molecular Structure: THEOCHEM | 2006 | 4 Pages |
Abstract
Electronic structure of 1-[N-(4-Fluorophenyl)]naphthaldimine phenol-imine (1) and quinoid (2) tautomers in ground and excited states are presented. The density functional calculations predict the ground state of 1 to be 5.4 kJ molâ1 lower in energy owing to stronger O-Hâ¯N (1.638 Ã
) interactions relative to Oâ¯H-N (1.651 Ã
) interactions in 2. The influence of solvents on the tautomeric stability as revealed from the self-consistent reaction field (SCRF) calculations suggests tautomer 2 to be of lower energy in protic polar solvents. Time-dependent density functional (TDDFT) calculations on the other hand bring about the reversal of relative stabilization and facilitate the tautomer 2 to be 6.6Â kJÂ molâ1 lower in energy in the lowest excited state which results from the extended conjugation owing to its planar geometry.
Keywords
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Physical Sciences and Engineering
Chemistry
Physical and Theoretical Chemistry
Authors
Nilesh R. Dhumal, Shridhar P. Gejji,