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Existence of dynamic tautomerism and divalent N(I) character in N ‐(pyridin‐2‐yl)thiazol‐2‐amine
Author(s) -
Bhatia Sonam,
Malkhede Yogesh J.,
Bharatam Prasad V.
Publication year - 2013
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.23293
Subject(s) - tautomer , chemistry , divalent , protonation , thiazole , pyridine , lone pair , amine gas treating , character (mathematics) , computational chemistry , quantum chemical , stereochemistry , crystallography , medicinal chemistry , molecule , organic chemistry , mathematics , ion , geometry
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.