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Updated: Mar 9, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
Published on: July 19, 2019
Excited-State Intramolecular Proton Transfer and Global Aromaticity
Naoko Nishina1, Toshiki Mutai2, Jun-Ichi Aihara1
1Department of Chemistry, Faculty of Science, Shizuoka University , Oya, Shizuoka 422-8529, Japan.
Abstract:
A general survey of excited-state intramolecular proton transfer (ESIPT) processes was made from the viewpoint of global aromaticity. For most ESIPT processes studied, a tautomeric product in the first excited electronic state was found to have a larger topological resonance energy (TRE) than the reactant in the same excited state. Conversely, if a transient tautomer is much less aromatic in the excited state than the reactant, an appreciable aromaticity-imposed energy barrier to the reaction will result. Thus, excited-state aromaticity is a very important factor, although not a definitive one, in determining the allowedness of ESIPT.
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