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The influence of secondary interactions on complex stability and double proton transfer reaction in 2-[1H]-pyridone/2-hydroxypyridine dimers

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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 NH2 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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Acknowledgments

Financial support from the Polish Ministry of Science and Higher Education (grant no. N N204 174138) is gratefully acknowledged. The authors are very much indebted to the CYFRONET in Cracow for providing computer time and programs. The author thanks Prof. Ryszard Gawinecki for discussion and suggestions during composing this paper.

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  1. Faculty of Chemical Technology and Engineering, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326, Bydgoszcz, Poland

    Borys Ośmiałowski & Robert Dobosz

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  1. Borys Ośmiałowski
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Correspondence to Borys Ośmiałowski.

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Ośmiałowski, B., Dobosz, R. The influence of secondary interactions on complex stability and double proton transfer reaction in 2-[1H]-pyridone/2-hydroxypyridine dimers. J Mol Model 17, 2491–2500 (2011). https://doi.org/10.1007/s00894-010-0934-y

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