Influence of the diol structure on the Lewis acidity of phenylboronates

Agnieszka Adamczyk-Woźniak , Michał Jakubczyk , Piotr Jankowski , Andrzej Sporzyński , Piotr M. Urbański

Abstract

A series of cyclic esters of pentafluorophenylboronic acid have been obtained and their Lewis acidity evaluated experimentally by a modified Gutmann method. The results based on 31P NMR measurements were compared with those determined by quantum mechanical calculations at the DFT-VSXC/pcS-2 level of theory. The differences in Lewis acidity are discussed on the basis of electronic and geometric parameters. The calculations revealed that the complexes of investigated esters with Et3PO have multiple conformers of a wide range of calculated 31P NMR shielding constants. Additionally, a correlation between the calculated O-B-O angle of esters and the experimental acceptor number was found. Copyright © 2013 John Wiley & Sons, Ltd.
Author Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Michał Jakubczyk (FC / DPC)
Michał Jakubczyk,,
- Department Of Physical Chemistry
, Piotr Jankowski (FC / CICSST)
Piotr Jankowski,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Andrzej Sporzyński (FC / DPC)
Andrzej Sporzyński,,
- Department Of Physical Chemistry
, Piotr M. Urbański (FC / DPC)
Piotr M. Urbański,,
- Department Of Physical Chemistry
Journal seriesJournal of Physical Organic Chemistry, ISSN 0894-3230, [1099-1395]
Issue year2013
Vol26
No5
Pages415-419
Publication size in sheets0.5
Keywords in Englishacceptor number ; boronic esters ; Laplacian ; NMR shielding constants calculation
ASJC Classification1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry
DOIDOI:10.1002/poc.3102
URL http://onlinelibrary.wiley.com/doi/10.1002/poc.3102/abstract
Languageen angielski
File
journalofphysicalorganicchemistry_2013_26_415.pdf 481.24 KB
Score (nominal)20
Score sourcejournalList
ScoreMinisterial score = 20.0, 31-01-2020, ArticleFromJournal
Ministerial score (2013-2016) = 20.0, 31-01-2020, ArticleFromJournal
Publication indicators Scopus Citations = 14; WoS Citations = 14; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.618; WoS Impact Factor: 2013 = 1.245 (2) - 2013=1.418 (5)
Citation count*12 (2015-11-15)
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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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