Influence of the ortho-methoxyalkyl substituent on the properties of phenylboronic acids

Agnieszka Adamczyk-Woźniak , Zbigniew Brzózka , Marek Dąbrowski , Izabela Madura , Roy Scheidsbach , Ewelina Tomecka , Kamil Żukowski , Andrzej Sporzyński

Abstract

Novel phenylboronic acids with methoxyalkyl groups at ortho position were synthesized. Molecular and crystal structures for two compounds were determined by single crystal X-ray diffraction. In both cases the O–H⋯O hydrogen-bonded dimers are the primary supramolecular motives in which the relatively short intramolecular B–O–H⋯O hydrogen bonds are observed between boronic group and oxygen atom of the ortho-substituent. Based on the CSD data for ortho-substitued boronic acids, the relation between the twist of the boronic moiety towards phenyl ring and the intramolecular H-bond angle is discussed. The intermolecular interactions between dimeric motives were investigated with the aid of Hirshfeld surface analysis. The weak C–H⋯O and C–H⋯π interactions were detected together with the agostic B⋯H ones. Sugar-binding ability of the methoxyalkyl compounds was evaluated for d-glucose, d-fructose and d-galactose by the competition assay with Alizarin Red S.
Author Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Zbigniew Brzózka (FC / IBC / DM)
Zbigniew Brzózka,,
- Department Of Microbioanalytics
, Marek Dąbrowski (FC / DPC)
Marek Dąbrowski,,
- Department Of Physical Chemistry
, Izabela Madura (FC / CICSST)
Izabela Madura,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Roy Scheidsbach (FC / DPC)
Roy Scheidsbach,,
- Department Of Physical Chemistry
, Ewelina Tomecka (FC / IBC / DM)
Ewelina Tomecka,,
- Department Of Microbioanalytics
, Kamil Żukowski (FC / IBC / DM)
Kamil Żukowski,,
- Department Of Microbioanalytics
, Andrzej Sporzyński (FC / DPC)
Andrzej Sporzyński,,
- Department Of Physical Chemistry
Journal seriesJournal of Molecular Structure, ISSN 0022-2860
Issue year2013
Vol1035
Pages190-197
Publication size in sheets0.5
Keywords in EnglishBoronic acids, Hirshfeld surface analysis, Hydrogen bond, Sugar receptor activity, Weak interactions
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1607 Spectroscopy; 1602 Analytical Chemistry
DOIDOI:10.1016/j.molstruc.2012.09.049
URL http://www.sciencedirect.com/science/article/pii/S0022286012008812
Languageen angielski
File
1-s2.0-S0022286012008812-main.pdf 1.05 MB
Score (nominal)20
Score sourcejournalList
ScoreMinisterial score = 20.0, 28-04-2020, ArticleFromJournal
Ministerial score (2013-2016) = 20.0, 28-04-2020, ArticleFromJournal
Publication indicators WoS Citations = 10; Scopus Citations = 12; GS Citations = 9.0; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.843; WoS Impact Factor: 2013 = 1.599 (2) - 2013=1.585 (5)
Citation count*9 (2016-06-01)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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