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Synthesis, structure and acidity constants of ligated α‐boryl acetic acids

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 with N‐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.

Authors:   Dennis P. Curran, Thomas Allen, steven geib, Stephen Weber, Anthony Robert Horner
Journal:   Chemistry - A European Journal
Year:   2017
Pages:   n/a
DOI:   10.1002/chem.201705754
Publication date:   05-Dec-2017
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