15N NMR study of (E)- and (Z)-2-(2-(2-hydroxy-4-nitrophenyl)hydrazono)-1-phenylbutane-1,3-diones. A suitable method for analysis of hydrazone isomers

Add time:08/17/2019    Source:sciencedirect.com

The one- and two-dimensional 15N NMR spectra of (E)- and (Z)-2-(2-(2-hydroxy-4-nitrophenyl)hydrazono)-1-phenylbutane-1,3-diones (1) were measured and analysed and 15N chemical shifts and 1J (15N, 1H) coupling constants were used for characterization of these two compounds from the viewpoint of azo-hydrazo tautomerism. Both compounds exist completely in appropriate hydrazo forms in dimethyl sulfoxide.Advantages of 15N NMR spectroscopy application in determination of acidic proton positions and azo-hydrazo content determination are discussed. We would like to propose the application of 15N NMR data measured at the natural abundance level of 15N as the “first glance” and strongest evidence method for the existence of hydrazo form in azo dyes and for differentiation of E- and Z-isomers around C=Nβ double bond.

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