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Analysis of the effects of N-substituents on some aspects of the aromaticity of imidazoles and pyrazoles

AuthorsCurutchet, C.; Poater, J.; Solà, Miquel; Elguero, José
Issue Date2011
PublisherAmerican Chemical Society
CitationThe journal of physical chemistry, A, Molecules, spectroscopy, kinetics, environment & general theory 115: 8571- 8577 (2011)
AbstractThe influence of the N-substituent on the aromaticity of azoles is a subject that has not yet been addressed in detail, in contrast to the good understanding of the corresponding C-substitution. In the present work, we analyze the aromaticities of a series of 1,2- and 1,3-azoles (pyrazoles and imidazoles, respectively) with the N-substituents NH2, OH, Cl, SH, H, NO2, CN, SO2F, SO2CF3, and N(SO2CF3)2, which are also compared with the aromaticities of the corresponding substituted benzene series. The larger stabilitiy of the imidazole ring is due not to a higher aromaticity, but rather to the weakness of the N-N bond in the pyrazole series. The aromaticity of azoles was found to be significantly less robust to N-substitutions than that of their C-substituted benzene counterparts. © 2011 American Chemical Society.
Identifiersdoi: 10.1021/jp204263p
issn: 1089-5639
Appears in Collections:(IQM) Artículos
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