Abstract
The paper describes microsynthesis and GC/EIMS analysis of O,O-dialkyl-N,N-dialkylphosphoramidates (DADAPs). DADAPs belong to schedule 2B6 category of chemical weapons convention (CWC), as they are important markers of the chemical warfare agent Tabun and its analogues. The study was undertaken to develop a spectral database of DADAPs for verification of CWC. The reported synthetic strategy can be adopted to prepare several analogues of DADAPs simultaneously and rapidly during official proficiency tests, for the unambiguous identification of analytes within a short period. Based on the EIMS data of more than 60 compounds, fragmentation routes are proposed which explain the formation of most of the characteristic fragment ions. Subtle differences in EIMS of isomeric DADAPs are discussed to facilitate their identification.
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References
Convention on the Prohibition of the Development, Production, Stockpiling and use of Chemical Weapons and their Destruction, Technical Secretariat of the Organisation for Prohibition of Chemical Weapons (1997) The Hague. Accessible through internet http://www.opcw.nl
Krutzsch W, Trapp RA (1994) Commentary of CWC. Martinus Nijhoff, The Netherlands
Mesilaakso M, Ratio M (2000) Encyclopedia of analytical chemistry. Wiley, Chichester, p 899
Kostiainen O (2000) Analysis of chemicals related to the chemicals weapons conventions. In: Bogusz MJ (ed) Forensic science, handbook of analytical separations, vol 2. Elsevier, Amsterdam, p 405
Hooijshuur EWJ, Hulst AG, De Jong Ad L, De Reuver LP, Van Krimpen SH, Van Baar BLM, Wils ERJ, Kientz CE, Brinkman UATh (2002) Trends Anal Chem 21(2):116–130
Criteria for Acceptable Performance of Laboratories in Proficiency Testing, Conference of the State Parties OPCW (1997) The Hague, C-I/DEC.62, 22 May 1997
Criteria for Designation of Laboratories (1997) OPCW-C-I/DEC.61, 22 May 1997
Standard Operating Procedures (SOP) for Evaluation of Results of OPCW Proficiency Test- S/46/98,dated 21 April 1998
Central OPCW Analytical Database (2003) Version 4, released on June 2003. Technical Secretariat of OPCW, The Hague
Wils ERJ, Fresenius J (1990) Anal Chem 338:22–27
Reddy TJ, Mirza SP, Sarathi UVR, Rao VJ, Vairamani M (2003) Rapid Comm Mass Spectrom 17:746–752
Durst HD, Mays JR, Ruth JL, Williams BR, Duevel RV (1998) Anal Lett 31(8):1429–1444
Black RM, Muir B (2003) J Chromatogr A 1000:253–281
Hooijschuur EWJ, Kientz CE, Brinkman UA (2002) J Chromatogr A 982:177–200
Hook GL, Kimm G, Koch D, Savage PB, Ding BW, Smith PA (2003) J Chromatogr A 992:1–9
Witkiewicz Z, Mazurek M, Szulc J (1990) J Chromatogr 503:293–357
Wils ERJ (2000) Gas chromatography/mass spectrometry in analysis of chemicals related to the chemicals weapons convention. In: Meyers RA (ed) Encyclopedia of analytical chemistry. Wiley, Chichester, p 979
Black RM, Harrison JM (1996) In: Hartley FR (ed) The chemistry of organophosphorus compounds. Wiley Interscience, Chichester
Kientz ChE (1998) J Chromatogr A 814:1–23
D’Augustino PA, Provost LR (1992) J Chromatogr 598:89–95
D’Augustino PA, Provost LR, Looye M (1989) J Chromatogr 465:271–283
D’Augustino PA, Hansen AS, Lockwood PA, Provost LR (1985) J Chromatogr 257:257–266
Organic Synthesis Collective (1973) Vol 5. Wiley, New York, p 758
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Palit, M., Pardasani, D., Gupta, A.K. et al. Microsynthesis and electron ionisation mass spectrometric analysis of chemical weapons convention (CWC)-related O,O-dialkyl-N,N-dialkylphosphoramidates. Anal Bioanal Chem 381, 477–486 (2005). https://doi.org/10.1007/s00216-004-2873-x
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DOI: https://doi.org/10.1007/s00216-004-2873-x