Literature DB >> 23978747

Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters.

Agnieszka Adamczyk-Woźniak1, Krzysztof M Borys, Karolina Czerwińska, Błażej Gierczyk, Michał Jakubczyk, Izabela D Madura, Andrzej Sporzyński, Ewelina Tomecka.   

Abstract

Catechol esters of ortho-methoxyalkylphenylboronic acids have been synthesized and characterized by (17)O NMR spectroscopy. The results were compared with the data for the parent acids. The influence of intramolecular and intermolecular hydrogen bonds on the properties of the boronic acids has been discussed. The (17)O NMR data for the boronic esters proved that there are no O → B interactions in the investigated compounds. This fact is connected with weak Lewis acidity of the parent acids and their low sugars' receptors activity. Crystal structure of ortho-methoxyphenylboronic acid catechol ester was determined.
Copyright © 2013 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  (17)O NMR; Boronic acids; Boronic esters; Hydrogen bond

Mesh:

Substances:

Year:  2013        PMID: 23978747     DOI: 10.1016/j.saa.2013.07.091

Source DB:  PubMed          Journal:  Spectrochim Acta A Mol Biomol Spectrosc        ISSN: 1386-1425            Impact factor:   4.098


  2 in total

1.  Boronic acids facilitate rapid oxime condensations at neutral pH.

Authors:  Pascal Schmidt; Cedric Stress; Dennis Gillingham
Journal:  Chem Sci       Date:  2015-04-13       Impact factor: 9.825

2.  (Trifluoromethoxy)Phenylboronic Acids: Structures, Properties, and Antibacterial Activity.

Authors:  Agnieszka Adamczyk-Woźniak; Jan T Gozdalik; Ewa Kaczorowska; Krzysztof Durka; Dorota Wieczorek; Dorota Zarzeczańska; Andrzej Sporzyński
Journal:  Molecules       Date:  2021-04-01       Impact factor: 4.411

  2 in total

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