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Updated: Jun 5, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
Published on: July 19, 2019
The influence of secondary interactions on complex stability and double proton transfer reaction in
Borys Ośmiałowski1, Robert Dobosz
1Faculty of Chemical Technology and Engineering, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland. borys.osmialowski@utp.edu.pl
Abstract:
The 2-[1H]-pyridone/2-hydroxypyridine tautomeric pair and its 6-substituted complexes have been studied with the use of DFT(M05) method. The intermolecular interaction energy has been calculated and discussed in the light of secondary interaction concept. The attractive secondary interactions of O/NH and O/OH type and OH/NH and OH/OH repulsions have been analyzed in terms of stabilizing or destabilizing influence on intermolecular behavior. The transition states of the double proton transfer reaction have been found and the energy of activation has been determined. The activation energy of the proton transfer reaction, geometry of the complexes and transition states show NH(2) and/or OH groups influence the properties of complexes and transition states. The HOMA index of aromaticity was applied to describe the π-electron delocalization in the heterocyclic rings.
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