Divalent N(I) Character in 2‑(Thiazol-2-yl)guanidine: An Electronic Structure Analysis

Several medicinally important compounds carry a 2-(thiazol-2-yl)guanidine unit. These species are generally (erroneously) represented as 1-(thiazol-2-yl)guanidine species. Quantum chemical studies were performed to identify the appropriate tautomeric state of this class of compounds. B3LYP/6-31+G(d)...

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Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2012-09, Vol.116 (36), p.9071-9079
Main Authors: Bhatia, Sonam, Bagul, Chandrakant, Kasetti, Yoganjaneyulu, Patel, Dhilon S, Bharatam, Prasad V
Format: Article
Language:English
Subjects:
Computer Simulation
Electronic structure
Electrons
Guanidines - chemistry
Mathematical models
Models, Molecular
Nitrogen - chemistry
Physical chemistry
Protonation
Quantum chemistry
Spectroscopy
Thiazoles - chemistry
Valence
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Summary:Several medicinally important compounds carry a 2-(thiazol-2-yl)guanidine unit. These species are generally (erroneously) represented as 1-(thiazol-2-yl)guanidine species. Quantum chemical studies were performed to identify the appropriate tautomeric state of this class of compounds. B3LYP/6-31+G(d) calculations indicate the preferred tautomeric state of these species is associated with the 2-(thiazol-2-yl)guanidine structure rather than the 1-(thiazol-2-yl)guanidine structure. G2MP2 calculations on the model system were carried out to study the electronic structure, electron delocalization, and protonation energy; MESP, ELF, HOMA, AIM, and NBO analyses were also carried out. The results indicate that this class of compounds may be treated as species with hidden ::N(←L)R character. Upon protonation of the thiazole ring nitrogen, these systems show the electronic structure as in ::N(←L)2 ⊕ systems with divalent N(I) oxidation state.
ISSN:1089-5639
1520-5215
DOI:10.1021/jp304789u