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

43 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

Access to Document

10.1021/acs.joc.7b01755

Cite this

@article{ed597fbedb8946daa08f7d5ebe9174ad,

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).",

author = "Zhen Li and Xin Li and Cheng, {Jin Pei}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = sep,

day = "15",

doi = "10.1021/acs.joc.7b01755",

language = "英语",

volume = "82",

pages = "9675--9681",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - An Acidity Scale of Triazolium-Based NHC Precursors in DMSO

AU - Li, Zhen

AU - Li, Xin

AU - Cheng, Jin Pei

PY - 2017/9/15

Y1 - 2017/9/15

N2 - 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).

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).

UR - http://www.scopus.com/inward/record.url?scp=85029507497&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b01755

DO - 10.1021/acs.joc.7b01755

M3 - 文章

C2 - 28837333

AN - SCOPUS:85029507497

SN - 0022-3263

VL - 82

SP - 9675

EP - 9681

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

An Acidity Scale of Triazolium-Based NHC Precursors in DMSO

Abstract

Access to Document

Other files and links

Fingerprint

Cite this