Document Detail


Trimethylsilyl transfer during electron ionization mass spectral fragmentation of some omega-hydroxycarboxylic and omega-dicarboxylic acid trimethylsilyl derivatives and the effect of chain length.
MedLine Citation:
PMID:  15329853     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The electron ionization (EI) mass spectral fragmentation of omega-hydroxycarboxylic and omega-dicarboxylic acid trimethylsilyl derivatives was investigated. The mass spectra of these compounds exhibited fragment ions resulting from classical fragmentation of the trimethylsilyl ether and ester groups, and others resulting from the interactions between the two functionalities (m/z 147, 204, 217, [M-31](+) and [M-105](+) in the case of omega-hydroxycarboxylic acid derivatives and m/z 147, 204, 217 and [M-131](+) in the case of omega-dicarboxylic acid derivatives). Several fragmentation pathways were proposed to explain the formation of these different fragment ions. It is proposed that the ions at m/z 204 and 217 are formed via an initial trimethylsilyl transfer between the ether and the ester group or between the two ester groups. This transfer appeared to be more favoured in the case of omega-dicarboxylic acid derivatives and to be dependent on the chain length. A more efficient transfer was in fact observed for compounds with a relatively long alkyl chain. In the case of shorter omega-hydroxycarboxylic and omega-dicarboxylic acid trimethylsilyl derivatives the formation of the ions at m/z 204 and 217 suffers strongly from competition from production of the ion at m/z 147.
Authors:
J-F Rontani; C Aubert
Related Documents :
17048123 - Facile synthesis of optically pure (s)-3-p-hydroxyphenyllactic acid derivatives.
7575653 - Behavior of n-acylated daunorubicins in mdr1 gene transfected and parental cells.
11693933 - Industrial scale production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate).
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  18     ISSN:  0951-4198     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2004  
Date Detail:
Created Date:  2004-08-26     Completed Date:  2004-10-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  1889-95     Citation Subset:  IM    
Copyright Information:
Copyright 2004 John Wiley & Sons, Ltd.
Affiliation:
Laboratoire de Microbiologie de Géochimie et d'Ecologie Marines (UMR 6117), Centre d'Océanologie de Marseille (OSU), Campus de Luminy-case 901, 13288 Marseille, France. rontani@com.univ-mrs.fr
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Carboxylic Acids / chemistry*
Spectrometry, Mass, Electrospray Ionization / methods*
Trimethylsilyl Compounds / chemistry*
Chemical
Reg. No./Substance:
0/Carboxylic Acids; 0/Trimethylsilyl Compounds

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Proteome analysis in the bovine adrenal medulla using liquid chromatography with tandem mass spectro...
Next Document:  Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry as a tool for fast iden...