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A theoretical NMR study of ortho and para ‐substituted benzenes compared with silabenzenes, pyridines and phosphabenzenes
Author(s) -
Alkorta Ibon,
Elguero José
Publication year - 2010
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2586
Subject(s) - chemistry , substituent , aromaticity , chemical shift , computational chemistry , stereochemistry , organic chemistry , molecule
Calculations of absolute shieldings and nuclear‐independent chemical shift [NICS(1)] values of 84 compounds (benzenes, silabenzenes, pyridines and phosphabenzenes) allowed to discuss the absolute shieldings in the function of Brown σ p + substituent constant and to predict 71 new chemical shifts. The NICS(1) analysis of the aromaticity leads to the unexpected result for the silabenzenes that it is almost insensitive to substituent effects. In these set of compounds, it can be concluded that the aromaticity and its sensitivity to substituent effects are orthogonal. Copyright © 2010 John Wiley & Sons, Ltd.

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