Premium
15 N n.m.r.: Substituent effects on nitrogen chemical shifts in anilinium ions
Author(s) -
Axenrod T.,
Wieder M. J.
Publication year - 1976
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270080705
Subject(s) - substituent , aniline , protonation , chemical shift , chemistry , lone pair , nitrogen , delocalized electron , ring (chemistry) , ion , medicinal chemistry , molecule , organic chemistry
15 N chemical shifts were measured in a series of anilinium fluorosulfonate salts and compared with chemical shift data from a comparable series of 15 N‐enriched aniline derivatives. A smaller overall range of nitrogen chemical shifts was observed for the protonated aniline series compared with that for the unprotonated anilines and is attributed to the elimination of nitrogen lone pair delocalization in the former series. Further‐more, it was found that the range of nitrogen chemical shifts in the protonated anilines is determined primarily by substituent electronic effects from the ortho ring position with almost negligible contributions from the para position.