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15N NMR: Substituent effect analysis in para-and meta-substituted phenylhydrazines

✍ Scribed by Elisabetta Mezzina; Fiammetta Ferroni; Domenico Spinelli; Stefano Chimichi; Vincenzo Frenna

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
552 KB
Volume
32
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^15^N NMR spectra of phenylhydrazine and of 14 para‐ and meta‐substituted phenylhydrazines were measured at natural isotope abundance in DMSO‐d~6~ solution. The substituent present exerts a larger influence on the chemical shift of the nitrogen atom directly bound to the aromatic ring (N‐1) than on the second one (N‐2), which shows an attenuated and inverted trend. The chemical shifts of N‐1 and N‐2 give a good cross correlation in both series of compounds if p‐NO~2~ and m‐F derivatives are excluded from the correlations of para‐ and meta‐substituted phenylhydrazines, respectively. Moreover, N‐1 SCS values show good linear correlations with Hammett substituent constants, with SCSs of directly bound hydrogen (H‐1) and with aniline nitrogen SCSs. The results of dual substituent parameter analysis are also reported together with a comparison of ^13^C and ^15^N chemical shifts with those of monosubstituted benzenes and substituted anilines.

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