Fluoro-substituted 2-formylphenylboronic acids: Structures, properties and tautomeric equilibria

Kornelia Kowalska , Agnieszka Adamczyk-Woźniak , Patrycja Gajowiec , Błażej Gierczyk , Ewa Kaczorowska , Łukasz Popenda , Grzegorz Schroeder , Artur Sikorski , Andrzej Sporzyński

Abstract

Four isomeric fluoro-2-formylphenylboronic acids were synthesized and characterized by 1H, 13C, 19F and 17O NMR. Molecular and crystal structure of two compounds was determined by single crystal XRD method. pKa values of all the isomers have been determined by spectrophotometric method and compared with the results for the corresponding benzoxaboroles as well as fluoro- and formylphenylboronic acids. Tautomeric equilibrium with cyclic benzoxaborole form was investigated. The influence of position of fluorine substituents on the properties of investigated compounds is discussed.
Author Kornelia Kowalska
Kornelia Kowalska,,
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, Agnieszka Adamczyk-Woźniak ZChF
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Patrycja Gajowiec ZChF
Patrycja Gajowiec,,
- Department Of Physical Chemistry
, Błażej Gierczyk
Błażej Gierczyk,,
-
, Ewa Kaczorowska ZChF
Ewa Kaczorowska,,
- Department Of Physical Chemistry
, Łukasz Popenda
Łukasz Popenda,,
-
, Grzegorz Schroeder
Grzegorz Schroeder,,
-
, Artur Sikorski
Artur Sikorski,,
-
, Andrzej Sporzyński ZChF
Andrzej Sporzyński,,
- Department Of Physical Chemistry
Journal seriesJournal of Fluorine Chemistry, ISSN 0022-1139
Issue year2016
Vol187
Pages1-8
Publication size in sheets0.5
Keywords in EnglishBoronic acid; Benzoxaborole; Fluorophenyl boronic acid; Crystal structure; Acidity; Tautomerism
DOIDOI:10.1016/j.jfluchem.2016.05.001
URL http://www.sciencedirect.com/science/article/pii/S0022113916301038
Languageen angielski
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1-s2.0-S0022113916301038-main.pdf 1.24 MB
Score (nominal)30
ScoreMinisterial score = 30.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 2.101 (2) - 2016=1.888 (5)
Citation count*0 (2016-06-01)
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