The influence of substituent field and resonance effects on the ease of N-heterocyclic carbene formation from imidazolium rings†,RSC Advances

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The influence of substituent field and resonance effects on the ease of N-heterocyclic carbene formation from imidazolium rings†
RSC Advances ( IF 3.9 ) Pub Date : 2018-04-18 00:00:00 , DOI: 10.1039/c8ra02526f
Wojciech P Oziminski _{1,

2} , Christopher A Ramsden ₃

Affiliation

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 (F) and resonance (R) substituent constants have been found. In all cases the field effect has the greatest influence but resonance effects are also significant.

中文翻译：

取代基场和共振效应对咪唑鎓环形成N-杂环卡宾容易程度的影响†

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介离子咪唑鎓-4-油酸盐去质子化容易程度的影响。已发现 CREF 值与 Swain 和 Lupton 场 ( F ) 以及共振 ( R ) 取代基常数之间存在显着相关性。在所有情况下，场效应的影响最大，但共振效应也很重要。

更新日期：2018-04-18

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