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
AbstractNovel 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.
|Journal series||Journal of Molecular Structure, ISSN 0022-2860|
|Publication size in sheets||0.5|
|Keywords in English||Boronic acids, Hirshfeld surface analysis, Hydrogen bond, Sugar receptor activity, Weak interactions|
|ASJC Classification||; ; ;|
|Score|| = 20.0, 28-04-2020, ArticleFromJournal|
= 20.0, 28-04-2020, ArticleFromJournal
|Publication indicators||= 10; = 12; = 9.0; : 2013 = 0.843; : 2013 = 1.599 (2) - 2013=1.585 (5)|
|Citation count*||9 (2016-06-01)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.