Consequences of one-electron oxidation and one-electron reduction for 4-aminopyrimidine--DFT studies.

Journal of Molecular Modeling
Ewa D RaczyńskaTomasz M Stępniewski

Abstract

The consequences of one-electron oxidation and one-electron reduction were studied for 4-aminopyrimidine (4APM), which displays prototropic tautomerism. Since experimental techniques are incapable of detecting less than 0.1% of minor tautomers, quantum-chemical calculations [DFT(B3LYP)/6-311+G(d,p)] were carried out for all possible tautomers of neutral 4AMP and its redox forms, 4APM (+ •) and 4APM (- •). Four tautomers were considered: one amine and three imine tautomers (two NH and one CH form). Geometric isomerism of the exo = NH group was also taken into account. One-electron oxidation (4APM - e → 4APM  (+ •)) has no significant effect on the tautomeric preferences; it influences solely the composition of the tautomeric mixture. The amine tautomer is favored for both 4APM  (+ •) and 4APM. An interesting change in the tautomeric preference occurs for 4APM (- •). One-electron reduction (4APM + e → 4APM (- •)) favors the C5 atom for the labile proton. The preference of the imine CH tautomer in the tautomeric mixture of 4APM (- •) may partially explain the origin of CH tautomers in nucleobases.

References

Jul 10, 1998·Biochimica Et Biophysica Acta·A Schellenberger
Jun 8, 2004·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Milen RaytchevTorsten Fiebig
Oct 13, 2005·Chemical Reviews·Ewa Daniela RaczyńskaRyszard Gawinecki
Dec 16, 2005·The Journal of Physical Chemistry. a·Maciej HarańczykMaciej Gutowski
May 6, 2006·The Journal of Organic Chemistry·Borys OśmiałowskiTadeusz M Krygowski
Oct 13, 2006·Bioorganic & Medicinal Chemistry Letters·Venkat R GadhachandaYun He
Mar 6, 2007·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Teruyoshi KitamuraAkira Fujimoto
Mar 16, 2007·Proceedings of the National Academy of Sciences of the United States of America·Maciej HarańczykKit H Bowen
Jun 5, 2007·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Teruyoshi KitamuraAkira Fujimoto
May 7, 2010·Chemical Reviews·Anil Kumar, Michael D Sevilla
Mar 4, 2011·Journal of Molecular Modeling·Ewa D RaczyńskaKatarzyna Kolczyńska
Aug 13, 2011·The Journal of Physical Chemistry. a·Lauri LippingIlmar A Koppel

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Citations

May 16, 2012·Journal of Molecular Modeling·Ewa D RaczyńskaKatarzyna Kolczyńska
Jun 5, 2016·Journal of Molecular Modeling·Ewa D RaczyńskaMariusz Sapuła
Oct 16, 2016·Chemical Reviews·Ewa D RaczyńskaPierre-Charles Maria
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alisa D KharlamovaIrina P Beletskaya
May 2, 2014·Chemical Reviews·Tadeusz M KrygowskiMarcin Palusiak
Jan 26, 2013·The Journal of Physical Chemistry. a·Ewa D RaczyńskaMałgorzata Hallmann

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