A Reconsideration of the Validity of Correlating Substituent-induced Proton Chemical Shifts in Aromatic Derivatives with Reactivity Parameters
作者:
Daniel A. Dawson,
Gordon K. Hamer,
William F. Reynolds,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1974)
卷期:
Volume 52,
issue 1
页码: 39-45
ISSN:0008-4042
年代: 1974
DOI:10.1139/v74-006
出版商: NRC Research Press
数据来源: NRC
摘要:
Comparisons of1H chemical shifts and charge densities (determined by CNDO/2 MO calculations) for 4-substituted derivatives of styrene, toluene, benzylchloride, andN,N,N-trimethylphenylammonium ion indicate that the chemical shifts primarily reflect intramolecular electronic effects. These effects are reflected by correlations of1H chemical shifts with theFandRreactivity parameters of Swain and Lupton. It is concluded that it is valid to correlate substituent-induced chemical shifts for aromatic derivatives with divided reactivity parameters provided that (1) chemical shifts are measured at infinite dilution in a non-polar medium and (2) at least ten derivatives of each family are investigated.Calculations for 4-substituted toluenes indicate that there will be a small conformational dependence for substituent-induced benzylic proton chemical shifts.
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