Divalent N(I) character in 2-(thiazol-2-yl)guanidine: an electronic structure analysis.
J Phys Chem A
; 116(36): 9071-9, 2012 Sep 13.
Article
em En
| MEDLINE
| ID: mdl-22920939
ABSTRACT
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 hiddenN(âL)R character. Upon protonation of the thiazole ring nitrogen, these systems show the electronic structure as inN(âL)2(â) systems with divalent N(I) oxidation state.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Tiazóis
/
Simulação por Computador
/
Elétrons
/
Guanidinas
/
Nitrogênio
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article