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15N NMR chemical shifts of ring substituted benzonitriles

✍ Scribed by Petr Žáček; Alk Dransfeld; Otto Exner; Jan Schraml

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
255 KB
Volume
44
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^15^N chemical shifts in an extensive series of para (15) and meta (15) as well as ortho (8) substituted benzonitriles, XC~6~H~4~CN, were measured in deuteriochloroform solutions, using three different methods of referencing. The standard error of the average chemical shift was less than 0.03 ppm in most cases. The results are discussed for both empirical correlations with substituent parameters and quantum chemical calculations. The ^15^N chemical shifts calculated at the GIAO/B3LYP/6–31 + G*//B3LYP/6–31 + G* level reproduce the experimental values well, and include nitrogen atoms in the substituent groups (range of 300 ppm with slope 0.98 and R = 0.998, n = 43). The ^15^N shifts in hydroxybenzonitriles are affected by interaction with the OH group. Therefore, these derivatives are excluded from the correlation analysis. The resultant ^15^N chemical shift correlates well with substituent constants, both in the simple Hammett or DSP relationships and the ^13^C substituent‐induced chemical shifts of the CN carbon. Copyright © 2006 John Wiley & Sons, Ltd.

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