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取代基场效应和共振效应对由咪唑鎓环形成N-杂环卡宾的难易程度的影响。

The influence of substituent field and resonance effects on the ease of N-heterocyclic carbene formation from imidazolium rings.

作者信息

Oziminski Wojciech P, Ramsden Christopher A

机构信息

National Medicines Institute 30/34 Chełmska Street 00-725 Warsaw Poland.

Faculty of Pharmacy, Medical University of Warsaw 1 Banacha Street 02-097 Warsaw Poland.

出版信息

RSC Adv. 2018 Apr 18;8(27):14833-14837. doi: 10.1039/c8ra02526f.

Abstract

Using a set of twelve selected substituents, the influence of substituent properties on the ease of deprotonation of imidazolium cations and mesoionic imidazolium-4-olates measured by the CREF index has been investigated. Significant correlations between CREF values and the Swain and Lupton field () and resonance () substituent constants have been found. In all cases the field effect has the greatest influence but resonance effects are also significant.

摘要

使用一组十二个选定的取代基,研究了取代基性质对通过CREF指数测量的咪唑鎓阳离子和中离子型咪唑-4-醇盐去质子化难易程度的影响。已发现CREF值与斯温(Swain)和卢普顿(Lupton)的场()和共振()取代基常数之间存在显著相关性。在所有情况下,场效应的影响最大,但共振效应也很显著。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca70/9079947/d9a4656fd7fb/c8ra02526f-f1.jpg

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