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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Atmospheric chemistry of diethyl methylphosphonate, diethyl ethylphosphonate, and triethyl phosphate.

Rate constants for the reactions of OH radicals and NO(3) radicals with diethyl methylphosphonate [DEMP, (C(2)H(5)O)(2)P(O)CH(3)], diethyl ethylphosphonate [DEEP, (C(2)H(5)O)(2)P(O)C(2)H(5)], and triethyl phosphate [TEP, (C(2)H(5)O)(3)PO] have been measured at 296 +/- 2 K and atmospheric pressure of air using relative rate methods. The rate constants obtained for the OH radical reactions (in units of 10(-11) cm(3) molecule(-1) s(-1)) were as follows: DEMP, 5.78 +/- 0.24; DEEP, 6.45 +/- 0.27; and TEP, 5.44 +/- 0.20. The rate constants obtained for the NO(3) radical reactions (in units of 10(-16) cm(3) molecule(-1) s(-1)) were the following: DEMP, 3.7 +/- 1.1; DEEP, 3.4 +/- 1.4; and TEP, 2.4 +/- 1. 4. For the reactions of O(3) with DEMP, DEEP, and TEP, an upper limit to the rate constant of <6 x 10(-20) cm(3) molecule(-1) s(-1) was determined for each compound. Products of the reactions of OH radicals with DEMP, DEEP, and TEP were investigated using in situ atmospheric pressure ionization mass spectrometry (API-MS) and, for the TEP reaction, gas chromatography with flame ionization detection (GC-FID) and in situ Fourier transform infrared (FT-IR) spectroscopy. The API-MS analyses show that the reactions are analogous, with formation of one major product from each reaction: C(2)H(5)OP(O)(OH)CH(3) from DEMP, C(2)H(5)OP(O)(OH)C(2)H(5) from DEEP, and (C(2)H(5)O)(2)P(O)OH from TEP. The FT-IR and GC-FID analyses showed that the major products (and their molar yields) from the TEP reaction are (C(2)H(5)O)(2)P(O)OH (65-82%, initial), CO(2) (80 +/- 10%), and HCHO (55 +/- 5%), together with lesser yields of CH(3)CHO (11 +/- 2%), CO (11 +/- 3%), CH(3)C(O)OONO(2) (8%), organic nitrates (7%), and acetates (4%). The probable reaction mechanisms are discussed.[1]


  1. Atmospheric chemistry of diethyl methylphosphonate, diethyl ethylphosphonate, and triethyl phosphate. Aschmann, S.M., Tuazon, E.C., Atkinson, R. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
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