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Microsynthesis and mass spectral study of Chemical Weapons Convention related 2‐alkyl‐1,3,6,2‐dioxathiaphosphocane‐2‐oxides
Author(s) -
Palit Meehir,
Mallard W. Gary,
Yang Imsuk
Publication year - 2008
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.3566
Subject(s) - chemistry , alkyl , protonation , fragmentation (computing) , electrospray ionization , mass spectrum , electron ionization , mass spectrometry , chemical ionization , ionization , medicinal chemistry , organic chemistry , photochemistry , ion , chromatography , computer science , operating system
Chemical Weapons Convention (CWC)‐related compounds where the phosphorus atom is part of a ring have very limited representation in mass spectral libraries and the open literature. Here we report electron ionization (EI), chemical ionization (CI) and electrospray ionization tandem mass spectrometry (ESI‐MS n ) spectra and retention indices for 2‐alkyl‐1,3,6,2‐dioxathiaphosphocane‐2‐oxides (alkyl C 1 to C 3 ) which are new cyclic chemicals covered under the CWC. The EI mass spectra show a pattern of ion fragmentation that is similar to that of other cyclic phosphonates in that loss of the alkylphosphonic acid as a neutral loss is more important than the presence of the protonated alkylphosphonic acid. In contrast to other cyclic phosphonates, the 2‐alkyl‐1,3,6,2‐dioxathiaphosphocane‐2‐oxides show almost no protonated alkylphosphonic acid and as a result the spectra do not carry the same distinctive signature of the phosphorus–carbon bond that is required for the chemical to be covered under the CWC. Copyright © 2008 John Wiley & Sons, Ltd.