Synthesis, Structure, and Acidity Constants of Ligated α-Boryl Acetic Acids
Synthesis, Structure, and Acidity Constants of Ligated α-Boryl Acetic Acids
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连接α-硼基乙酸的合成、结构和酸度常数
DOI：
10.1002/chem.201705754
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Curran, Dennis P.
中科院分区：
文献类型：
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作者：
Allen, Thomas H.;Horner, Anthony R.;Geib, Steven J.;Weber, Stephen G.;Curran, Dennis P.
各种连接的α-硼基乙酸酯的碱性水解物提供了未知化合物BH2CH2CO2H的第一个连接的衍生物。以杂环卡宾、胺和吡啶为配体，合成了四个一元酸(L-BH_2CH_2CO_2H)和一个二元酸(L-BH(CH_2CO_2H)_2)。用X-射线单晶衍射法和酸度常数(PKA)法对其进行了表征。它们是所有已知的羧酸中酸性最弱的。反过来，它们的共轭碱基是所有羧酸盐中最强的。
Basic hydrolyses of various ligated α‐boryl acetic acid esters provided the first ligated derivatives of the unknown compound boroacetic acid (BH2CH2CO2H). Four monoacids (L‐BH2CH2CO2H) and one diacid (L‐BH(CH2CO2H)2) were prepared withN‐heterocyclic carbene, amine, and pyridine ligands (L). The stable acids were characterized by X‐ray crystallography and acidity constant (pKa) measurements. They rank among the least acidic of all known carboxylic acids. In turn, their conjugate bases are among the strongest of all carboxylates.