Silylation of acetaminophen by trifluoroacetamide-based silylation agents

Magda Caban , Piotr Stepnowski


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 (FCh / DEA / PAiMŚ)
Magda Caban,,
- Pracownia Analityki i Monitoringu Środowiska
, Piotr Stepnowski (FCh / DEA / LChER)
Piotr Stepnowski,,
- Laboratory of Chemical Environmental Risks
Journal seriesJournal of Pharmaceutical and Biomedical Analysis, ISSN 0731-7085, (A 35 pkt)
Issue year2018
Publication size in sheets0.5
Keywords in Englishacetaminophen, silylation, mass spectra interpretation, BSTFA, amide reaction
ASJC Classification1308 Clinical Biochemistry; 1607 Spectroscopy; 3002 Drug Discovery; 3003 Pharmaceutical Science; 1602 Analytical Chemistry
Languageen angielski
Score (nominal)35
Score sourcejournalList
ScoreMinisterial score = 35.0, 03-04-2020, ArticleFromJournal
Publication indicators Scopus Citations = 3; WoS Citations = 2; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 1.144; WoS Impact Factor: 2018 = 2.983 (2) - 2018=3.054 (5)
Citation count*4 (2020-04-03)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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