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

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...

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Detalles Bibliográficos
Autores principales: Oziminski, Wojciech P., Ramsden, Christopher A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9079947/
https://www.ncbi.nlm.nih.gov/pubmed/35541359
http://dx.doi.org/10.1039/c8ra02526f
Descripción
Sumario: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.

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