Existence of dynamic tautomerism and divalent N(I) character in N-(pyridin-2-yl)thiazol-2-amine

Authors

  • Sonam Bhatia,

    1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India
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  • Yogesh J. Malkhede,

    1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India
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  • Prasad V. Bharatam

    Corresponding author
    1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India
    • S. Bhatia, YJ. Malkhede and PV. Bharatam Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector-67, S. A. S. Nagar, Mohali, Punjab, 160 062, India Fax: (+91) 172 2214692 E-mail: pvbharatam@niper.ac.in

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Abstract

N-(Pyridin-2-yl)thiazol-2-amine is a versatile chemical functional unit present in many therapeutically important species. Quantum chemical analysis shows that there are six competitive isomeric structures possible for this class of compounds within a relative energy difference of ∼4 kcal/mol. Some of the isomeric structures possess divalent N(I) character. There appears to be a competition between the thiazole and pyridine groups to accommodate the tautomeric hydrogen, and consequently show electron donating property in the structure with R-N←L representation. Details of electron distribution, tautomeric preferences, protonation energy, and divalent N(I) character, and so on, of this class of compounds are presented in this article. Subsequently, upon protonation, (L→N←L) character is clearly evident in these moieties as molecular orbital analysis clearly shows two lone pairs of electrons on the central nitrogen, in this system. © 2013 Wiley Periodicals, Inc.

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