Mechanism of alkyl chloroformate-mediated esterification of carboxylic acids in aqueous media
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60077344%3A_____%2F21%3A00545751" target="_blank" >RIV/60077344:_____/21:00545751 - isvavai.cz</a>
Alternative codes found
RIV/00216275:25310/21:39917754
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c01546" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c01546</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.1c01546" target="_blank" >10.1021/acs.joc.1c01546</a>
Alternative languages
Result language
angličtina
Original language name
Mechanism of alkyl chloroformate-mediated esterification of carboxylic acids in aqueous media
Original language description
The protection of carboxyl groups by esterification has been the most common method in macroscale and microscale chemistries. The esterification is usually conducted under anhydrous conditions, however, in biological chemistry and related fields, the reaction is of major concern in aqueous environments. Immediate esterification of the carboxyl in aqueous alcoholic media driven by an alkyl chloroformate and pyridine has been such a method which has found widespread use in many research and industrial laboratories. Nevertheless, the reaction mechanism has not yet been investigated, to our knowledge, and is not well understood. Herein, we describe the reaction intermediates and demonstrate that the reaction proceeds via a continual formation of the N-acylpyridinium intermediate decomposed by several reaction channels to the final ester. The understanding of the mechanism could encourage novel laboratory applications of this important esterification method.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10609 - Biochemical research methods
Result continuities
Project
<a href="/en/project/GA17-22276S" target="_blank" >GA17-22276S: New methods for metabolomic analysis of hardly determined metabolites</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
86
Issue of the periodical within the volume
23
Country of publishing house
US - UNITED STATES
Number of pages
7
Pages from-to
16293-16299
UT code for WoS article
000752848600008
EID of the result in the Scopus database
2-s2.0-85115233780