Journal of Physical Chemistry p. 1243 - 1245 (1981)
Update date:2022-08-18
Topics:
Chuchani, Gabriel
Triana, Juana L.
Rotinov, Alexandra
Caraballo, Darlo F.
Several ethyl chloroesters were pyrolyzed in a static reactor in the presence of a propene inhibitor at temperatures between 360 and 420 deg C and pressures between 49 and 209 torr.The reactions are homogeneous, unimolecular, and follow a first-order rate law.The temperature dependence of the rate coefficients is given by the following Arrhenius equations: for ethyl chloroacetate, log k(s-1) = (12.70+/-0.50) - (197.0+/-6.1)kJ mol-1 (2.303RT)-1; for ethyl 3-chloropropionate, log k(s-1) = (12.54+/-0.22) - 196.8+/-2.7) kJ mol-1 (2.303RT)-1; and ethyl 4-chlorobutyrate, log k(s-1) = (12.67+/-0.31) - (198.7+/-3.8) kJ mol-1 (2.303RT)-1.The data from the rate coefficients give an approximate correlation only with ?* values (ρ*=0.357, r=0.903, and intercept =0.048 at 400 deg C).The present work together with those reported in the literature suggests, that electron-withdawing substituents at the acyl carbon of ethyl, isopropyl, and tert-butyl esters of substituted acetates enhance the rate of elimination, whereas electron-releasing substituents decrease it.
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