Silylation of acetaminophen by trifluoroacetamide-based silylation agents

Magda Caban , Piotr Stepnowski

Abstract

In the presented report, we have described the silylation reaction between the amide group in acetaminophen and a two most popular trifluoroacetamide-based silylation reagents – BSTFA and MSTFA. Both reagents had a amide groups on structures. An investigation was made through the performance of a set of experiments, GC–MS analysis, and a theoretical study, namely interpretation of mass spectra, presentation of the resonance states of all the involved compounds and SN2 reaction schemes, which was found to be different when BSTFA and MSTFA was applied. The negligible effect of used solvent was also described. The fragmentation of TMS-derivatives (MS spectra) was presented and it has confirmed our previous investigations with silylation of pharmaceuticals, and a general rules of fragmentation patterns. Thanks to this the structure of di-O,O-TMS-acetaminophen was proven.
Author Magda Caban PAiMŚ
Magda Caban,,
- Pracownia Analityki i Monitoringu Środowiska
, Piotr Stepnowski PChZŚ
Piotr Stepnowski,,
- Laboratory of Chemical Environmental Risks
Journal seriesJournal of Pharmaceutical and Biomedical Analysis, ISSN 0731-7085
Issue year2018
Vol154
Pages433-437
Publication size in sheets0.5
Keywords in Englishacetaminophen, silylation, mass spectra interpretation, BSTFA, amide reaction
DOIDOI:10.1016/j.jpba.2018.03.037
URL https://doi.org/10.1016/j.jpba.2018.03.037
Languageen angielski
Score (nominal)35
ScoreMinisterial score = 35.0, 15-05-2018, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 15-05-2018, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 3.255 (2) - 2016=2.953 (5)
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