title: Existence of dynamic tautomerism and divalent N(I) character in N-(pyridin-2-yl)thiazol-2-amine.
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.
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector-67, S. A. S. Nagar, Mohali, Punjab, 160 062, India.
authors.forename: Sonam
authors.initials: S
authors.lastname: Bhatia
authors.forename: Yogesh J
authors.initials: YJ
authors.lastname: Malkhede
authors.forename: Prasad V
authors.initials: PV
authors.lastname: Bharatam
mesh_terms: D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011789:Quantum Theory; D013844:Thiazoles / Q000737:chemistry*
chemical_list: C000591601:N-(pyridin-2-yl)thiazol-2-amine; D011725:Pyridines; D013844:Thiazoles