Equilibrium acidities of BINOL type chiral phenolic hydrogen bonding donors in DMSO

Xiang Ni; Xin Li; Zhen Li; Jin Pei Cheng

doi:10.1039/c6qo00252h

Equilibrium acidities of BINOL type chiral phenolic hydrogen bonding donors in DMSO

Xiang Ni
, Xin Li
, Zhen Li
, Jin Pei Cheng

Nankai University
Collaborative Innovation Center of Chemical Science and Engineering
Tsinghua University

科研成果: 期刊稿件 › 文章 › 同行评审

14 引用（Scopus）

摘要

The pK_a values of fifteen BINOL type chiral phenolic catalysts were determined by the overlapping indicator method in DMSO via UV spectrophotometric titrations. The acidities cover the range from 9.30 to 16.43. The pK_a gap between BINOL and 2-naphthol was explained by IR spectrum data, crystal structure and ¹H NMR. The relationship between the pK_a values of 3,3′-modified BINOLs and Hammett ortho substituent constants (σ_o ^-) was investigated and a good correlation (R² = 0.984) was obtained. The results may be helpful for the rational design and development of novel BINOL type phenolic catalysts, sensors and ligands.

源语言	英语
页（从-至）	1154-1158
页数	5
期刊	Organic Chemistry Frontiers
卷	3
期	9
DOI	https://doi.org/10.1039/c6qo00252h
出版状态	已出版 - 9月 2016
已对外发布	是

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title = "Equilibrium acidities of BINOL type chiral phenolic hydrogen bonding donors in DMSO",

abstract = "The pKa values of fifteen BINOL type chiral phenolic catalysts were determined by the overlapping indicator method in DMSO via UV spectrophotometric titrations. The acidities cover the range from 9.30 to 16.43. The pKa gap between BINOL and 2-naphthol was explained by IR spectrum data, crystal structure and 1H NMR. The relationship between the pKa values of 3,3′-modified BINOLs and Hammett ortho substituent constants (σo -) was investigated and a good correlation (R2 = 0.984) was obtained. The results may be helpful for the rational design and development of novel BINOL type phenolic catalysts, sensors and ligands.",

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

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T1 - Equilibrium acidities of BINOL type chiral phenolic hydrogen bonding donors in DMSO

AU - Ni, Xiang

AU - Li, Xin

AU - Li, Zhen

AU - Cheng, Jin Pei

PY - 2016/9

Y1 - 2016/9

N2 - The pKa values of fifteen BINOL type chiral phenolic catalysts were determined by the overlapping indicator method in DMSO via UV spectrophotometric titrations. The acidities cover the range from 9.30 to 16.43. The pKa gap between BINOL and 2-naphthol was explained by IR spectrum data, crystal structure and 1H NMR. The relationship between the pKa values of 3,3′-modified BINOLs and Hammett ortho substituent constants (σo -) was investigated and a good correlation (R2 = 0.984) was obtained. The results may be helpful for the rational design and development of novel BINOL type phenolic catalysts, sensors and ligands.

AB - The pKa values of fifteen BINOL type chiral phenolic catalysts were determined by the overlapping indicator method in DMSO via UV spectrophotometric titrations. The acidities cover the range from 9.30 to 16.43. The pKa gap between BINOL and 2-naphthol was explained by IR spectrum data, crystal structure and 1H NMR. The relationship between the pKa values of 3,3′-modified BINOLs and Hammett ortho substituent constants (σo -) was investigated and a good correlation (R2 = 0.984) was obtained. The results may be helpful for the rational design and development of novel BINOL type phenolic catalysts, sensors and ligands.

UR - https://www.scopus.com/pages/publications/84983611798

U2 - 10.1039/c6qo00252h

DO - 10.1039/c6qo00252h

M3 - 文章

AN - SCOPUS:84983611798

SN - 2052-4110

VL - 3

SP - 1154

EP - 1158

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 9

ER -

Equilibrium acidities of BINOL type chiral phenolic hydrogen bonding donors in DMSO

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