Influence of the diol structure on the Lewis acidity of phenylboronates
Agnieszka Adamczyk-Woźniak , Michał Jakubczyk , Piotr Jankowski , Andrzej Sporzyński , Piotr M. Urbański
AbstractA 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.
|Journal series||Journal of Physical Organic Chemistry, ISSN 0894-3230, [1099-1395]|
|Publication size in sheets||0.5|
|Keywords in English||acceptor number ; boronic esters ; Laplacian ; NMR shielding constants calculation|
|Score|| = 20.0, 31-01-2020, ArticleFromJournal|
= 20.0, 31-01-2020, ArticleFromJournal
|Publication indicators||= 14; = 14; : 2013 = 0.618; : 2013 = 1.245 (2) - 2013=1.418 (5)|
|Citation count*||12 (2015-11-15)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.