The tautomeric structures of 3(5),3′(5′)-azopyrazole [(E)-1,2-di(1H-pyrazol-3(5)-yl)diazene)]: The combined use of NMR and electronic spectroscopies with DFT calculations

• DOI: 10.1016/j.molstruc.2012.02.013
• Publication Date: 2012-02-16T06:46:19Z
• Authors: Pablo López-Tarifa; Goar Sánchez-Sanz; Ibon Alkorta; José Elguero; Dionisia Sanz; Almudena Perona; Rosa M. Claramunt
• Keywords: Pyrazole; Proton NMR; Conformational isomerism; Derivative (finance); Chemical shift; Coupling constant

Peer Reviewed<br/>An azo derivative of 1H-pyrazole has been chosen to study the information obtained from different techniques for determining the structure of a non-crystalline compound in the solid-state and in solution. Syn-anti isomerism of the azo group, prototropic tautomerism of the 1H-pyrazole and rotation about the pyrazole-azo group resulted in 20 structures that were analyzed. Energy calculations, 13C and 15N chemical shifts, 1H- 1H coupling constants and electronic spectra reduced the 20 possible structures to only one, the 3,3′-Z,Z-anti-azopyrazole. © 2012 Elsevier B.V. All rights reserved.<br/>