NDLI: On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes 2. Complexation and esterification of di- and tricarboxylic acids

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On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes 2. Complexation and esterification of di- and tricarboxylic acids

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Dalton Transactions Vol - 0 Issue - 7

Dalton Transactions Vol - 0 Issue - 6

Dalton Transactions Vol - 0 Issue - 5

On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes 2. Complexation and esterification of di- and tricarboxylic acids

Content Provider	Royal Society of Chemistry (RSC)
Author	Ansell, Richard J. Barrett, Simon A. Meegan, Jonathan E. Warrinner, Stuart L.
Copyright Year	2009
Abstract	The selective esterifications of L-malic, L-tartaric and citric acids with tetramethoxysilane Si(OMe)4, in methanol (MeOH) have been demonstrated for the first time. The interactions between these acids and Si(OMe)4, and also between oxalic acid and Si(OMe)4, were investigated using 1H, 13C and 29Si solution phase NMR, and electrospray mass spectrometry (ES-MS). Si(OMe)4 acts as a catalyst/reagent in the selective esterification of simple 2-hydroxycarboxylic acids (2HOAs), but with the di- and tri-carboxylic acids more complex selectivities are observed: the esterification of oxalic acid proceeds slower than in MeOH alone, L-malic acid is selectively esterified ∼1000 times faster at the 2-hydroxy acid, L-tartaric acid is esterified ∼1000 times faster to the mono- and diester, while citric acid is selectively methylated at the terminal (3-hydroxycarboxyl) groups ∼1000 times faster than in the absence of Si(OMe)4. Esterification is associated with the condensation of silane units to form oligomers. A mechanism is proposed in which 2HOAs attach to silicon via the alkoxy group and carboxyl groups to form various reactive cyclic intermediates. These intermediates may lead to accelerated esterification via nucleophilic attack of MeOH at the ligated carboxyl group, while a separate reaction pathway leads to condensation of silicon centres leading to oligosilanes. The mechanism has implications for the use of 2HOAs as templates in sol–gel silica preparation.
Starting Page	1460
Ending Page	1470
Page Count	11
File Format	HTM / HTML PDF
ISSN	14779226
Volume Number	0
Issue Number	8
Journal	Dalton Transactions
DOI	10.1039/b814488e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	MeOH Tetramethyl orthosilicate Methanol Carboxylic acid Nuclear magnetic resonance spectroscopy Electrospray ionization Mass spectrometry Reagent Ester Silane Silicon dioxide
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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