Journal of Physical Chemistry p. 551 - 552 (1985)
Update date:2022-08-24
Topics:
Chuchani, Gabriel
Rotinov, Alexandra
Martin, Ignacio
The kinetics of the gas-phase dehydrochlorination of several phenylalkyl chlorides were determined in a static system, seasoned with allyl bromide, and in the presence of the free radical inhibitor propene.The working temperature and pressure ranges were 398.8-480.6 deg C and 66-202 torr, respectively.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 3-chloro-1-phenylpropane, log k1 (s-1) = (13.99 +/- 0.26) - (238.4 +/- 3.5) kJ*mol-1; for 4-chloro-1-phenylbutane, log k1 (s-1) = (13.07 +/- 0.43) - (220.5 +/- 5.8) kJ*mol-1 (2.303RT)-1; and for 5-chloro-1-phenylpentane, log k1 (s-1) = (13.75 +/- 0.36) - (231.2 +/- 4.9) kJ*mol-1 (2.303RT)-1.When the rates of HCl elimination among each of the phenylalkyl chlorides are compared with those for the coresponding unsubstituted alkyl chloride, participation of the C6H5 group at the 3 position is more favored, while that at the 5 and 6 positions is rather weak.Participation of C6H5 group at the 4 position is apparently absent.
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