An Acidity Scale of Triazolium-Based NHC Precursors in DMSO

Zhen Li; Xin Li; Jin Pei Cheng

doi:10.1021/acs.joc.7b01755

An Acidity Scale of Triazolium-Based NHC Precursors in DMSO

Zhen Li
, Xin Li
, Jin Pei Cheng

Nankai University

科研成果: 期刊稿件 › 文章 › 同行评审

45 引用（Scopus）

摘要

An acidity scale of triazolium-based N-heterocyclic carbene precursors was established by measuring 25 compounds' (10a-15b) equilibrium acidities in dimethyl sulfoxide (DMSO) solution using overlapping indicator method. The pK_a values ranged from 12.08 to 15.5, responding not only to the N-aryl motif, but also to the core structure. Excellent correlation was observed between the pK_a values and the Hammett substituent constants (σ_p).

源语言	英语
页（从-至）	9675-9681
页数	7
期刊	Journal of Organic Chemistry
卷	82
期	18
DOI	https://doi.org/10.1021/acs.joc.7b01755
出版状态	已出版 - 15 9月 2017
已对外发布	是

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abstract = "An acidity scale of triazolium-based N-heterocyclic carbene precursors was established by measuring 25 compounds' (10a-15b) equilibrium acidities in dimethyl sulfoxide (DMSO) solution using overlapping indicator method. The pKa values ranged from 12.08 to 15.5, responding not only to the N-aryl motif, but also to the core structure. Excellent correlation was observed between the pKa values and the Hammett substituent constants (σp).",

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AB - An acidity scale of triazolium-based N-heterocyclic carbene precursors was established by measuring 25 compounds' (10a-15b) equilibrium acidities in dimethyl sulfoxide (DMSO) solution using overlapping indicator method. The pKa values ranged from 12.08 to 15.5, responding not only to the N-aryl motif, but also to the core structure. Excellent correlation was observed between the pKa values and the Hammett substituent constants (σp).

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An Acidity Scale of Triazolium-Based NHC Precursors in DMSO

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