ISSN:
0749-1581
Keywords:
13C NMR chemical shifts
;
15N NMR chemical shifts
;
15N substituent effects
;
Substituted phenylhydrazines
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
15N NMR spectra of phenylhydrazine and of 14 para- and meta-substituted phenylhydrazines were measured at natural isotope abundance in DMSO-d6 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-NO2 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 13C and 15N chemical shifts with those of monosubstituted benzenes and substituted anilines.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260320210
