Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters

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

Abstract

Catechol esters of ortho-methoxyalkylphenylboronic acids have been synthesized and characterized by 17O 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 17O 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.
Author Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Krzysztof M. Borys (FC / DPC)
Krzysztof M. Borys,,
- Department Of Physical Chemistry
, Karolina Czerwińska (FC / CICSST)
Karolina Czerwińska,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Błażej Gierczyk - [Adam Mickiewicz University (UAM)]
Błażej Gierczyk,,
-
- Uniwersytet im. Adama Mickiewicza w Poznaniu
, Michał Jakubczyk (FC / DPC)
Michał Jakubczyk,,
- Department Of Physical Chemistry
, Izabela Madura (FC / CICSST)
Izabela Madura,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Andrzej Sporzyński (FC / DPC)
Andrzej Sporzyński,,
- Department Of Physical Chemistry
, Ewelina Tomecka (FC / IBC / DM)
Ewelina Tomecka,,
- Department Of Microbioanalytics
Journal seriesSpectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, ISSN 1386-1425
Issue year2013
Vol116
Pages616-621
Publication size in sheets0.5
Keywords in Englishboronic acids, boronic esters, 17O NMR, hydrogen bond
ASJC Classification1607 Spectroscopy; 3105 Instrumentation; 3107 Atomic and Molecular Physics, and Optics; 1602 Analytical Chemistry
DOIDOI:10.1016/j.saa.2013.07.091
URL http://www.sciencedirect.com/science/article/pii/S1386142513008391
Languageen angielski
File
2-s2.0-S1386142513008391-main.pdf 558.12 KB
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 25.0, 09-01-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 09-01-2020, ArticleFromJournal
Publication indicators Scopus Citations = 5; WoS Citations = 5; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 1.154; WoS Impact Factor: 2013 = 2.129 (2) - 2013=2.163 (5)
Citation count*5 (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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