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The Cl‐atom‐initiated oxidation of two esters, ethyl formate [HC(O)OCH2CH3] and Ethyl acetate (cas 141-78-6) [CH3C(O)OCH2CH3], has been studied at pressures close to 1 atm as a function of temperature (249–325 K) and O2 partial pressure (50–700 Torr), using an environmental chamber technique. In both cases, Cl‐atom attack at the CH2 group is most important, leading in part to the formation of radicals of the type RC(O)OCH(O•)CH3 [R = H, CH3]. The atmospheric fate of these radicals involves competition between reaction with O2 to produce an anhydride compound, RC(O)OC(O)CH3, and the so‐called α‐ester rearrangement that produces an organic acid, RC(O)OH, and an acetyl radical, CH3C(O). For both species studied, the α‐ester rearrangement is found to dominate in air at 1 atm and 298 K. Barriers to the rearrangement of 7.7 ± 1.5 and 8.4 ± 1.5 kcal/mole are estimated for CH3C(O)OCH(O•)CH3 and HC(O)OCH(O•)CH3, respectively, leading to increased occurrence of the O2 reaction at reduced temperature. The data are combined with those obtained from similar studies of other simple esters to provide a correlation between the rate of occurrence of the α‐ester rearrangement and the structure of the reacting radical. © 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 397–413, 2010
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