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

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

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 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).

Original language	English
Pages (from-to)	9675-9681
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	82
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.7b01755
State	Published - 15 Sep 2017
Externally published	Yes

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10.1021/acs.joc.7b01755

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title = "An Acidity Scale of Triazolium-Based NHC Precursors in DMSO",

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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ER -

An Acidity Scale of Triazolium-Based NHC Precursors in DMSO

Abstract

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