Structures and properties of trifluoromethylphenylboronic acids

Jan Gozdalik , Paulina Marek , Izabela Madura , Błażej Gierczyk , Łukasz Popenda , Grzegorz Schroeder , Agnieszka Adamczyk-Woźniak , Andrzej Sporzyński

Abstract

Three isomers of trifluoromethylphenylboronic acids were synthesized and characterized by 1H, 13C, 11B and 19F NMR. The investigated compounds exhibit high resistance to protodeboronation reaction. Molecular and crystal structure of these compounds was determined by single crystal XRD method. The compounds form typical hydrogen-bonded dimers with the syn-anti conformation. CF3 substituent does not interact with boronic moiety neither as hydrogen bond acceptor nor a lone-electron pair donor. pKa values of the isomers have been determined by spectrophotometric and potentiometric method. Introduction of the CF3 group increases the acidity for meta and para isomers in comparison to the phenylboronic acid, while for the ortho isomer the acidity is reduced due to the steric hindrance.
Author Jan Gozdalik (FC / DPC)
Jan Gozdalik,,
- Department Of Physical Chemistry
, Paulina Marek (FC / CICSST)
Paulina Marek,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Izabela Madura (FC / CofIC)
Izabela Madura,,
- Chair Of Inorganic Chemistry
, Błażej Gierczyk - [Uniwersytet im. Adama Mickiewicza w Poznaniu]
Błażej Gierczyk,,
-
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, Łukasz Popenda - [Adam Mickiewicz University (UAM)]
Łukasz Popenda,,
-
- Uniwersytet im. Adama Mickiewicza w Poznaniu
, Grzegorz Schroeder - [Uniwersytet im. Adama Mickiewicza w Poznaniu]
Grzegorz Schroeder,,
-
-
, Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Andrzej Sporzyński (FC / DPC)
Andrzej Sporzyński,,
- Department Of Physical Chemistry
Journal seriesJournal of Molecular Structure, ISSN 0022-2860, (A 20 pkt)
Issue year2019
Vol1180
Pages237-243
Publication size in sheets0.5
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1607 Spectroscopy; 1602 Analytical Chemistry
DOIDOI:10.1016/j.molstruc.2018.11.090
URL https://www.sciencedirect.com/science/article/pii/S0022286018314030
Languageen angielski
File
1-s2.0-S0022286018314030-main.pdf 1.09 MB
Score (nominal)20
ScoreMinisterial score = 20.0, 30-04-2019, ArticleFromJournal
Ministerial score (2013-2016) = 20.0, 11-03-2019, ArticleFromJournal
Publication indicators Scopus Citations = 0; WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.751; WoS Impact Factor: 2017 = 2.011 (2) - 2017=1.784 (5)
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