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Perfluorinated Trialkoxysilanol with Dramatically Increased Brønsted Acidity
Author(s) -
Feige Felix,
Malaspina Lorraine A.,
Rychagova Elena,
Ketkov Sergey,
Grabowsky Simon,
Hupf Emanuel,
Beckmann Jens
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103177
Subject(s) - deprotonation , brønsted–lowry acid–base theory , chemistry , conjugate , conjugate acid , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , ion , mathematics , mathematical analysis
The Brønsted acidity of the perfluorinated trialkoxysilanol {(F 3 C) 3 CO} 3 SiOH is more than 13 orders of magnitude higher than that of orthosilicic acid, Si(OH) 4 , and even more for most previously known silanols. It is easily deprotonated by simple amines and pyridines to give the conjugate silanolates [OSi{OC(CF 3 ) 3 } 3 ] − , which possess extremely short Si−O bonds, comparable to those of silanones.