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The dissociation of 3-chloro-1-butene and the resonance energy of the chloro-allyl radical

✍ Scribed by A. B. Trenwith

Publisher
John Wiley and Sons
Year
1973
Tongue
English
Weight
448 KB
Volume
5
Category
Article
ISSN
0538-8066

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✦ Synopsis

Methane is a primary product of pyrolysis of 3-chloro-I-butene at temperatures in the range 776-835'K, and from its rate of formation values have been obtained for the limiting high-pressure rate constant of the reaction (1) CH$CHClCH=CHZ * .CH3 + .CHCICH=CHZ These may be represented by the expression log [(k,),/~ec-~] = (16.7 f 0.3) -(71.5 + 1.5)/8, where e = 2.303RT kcal/mole. Assuming a zero activation energy for the reverse reaction and that over the experimental temperature range the rates at which a methyl radical adds on to chlorobutene are comparable to those at which it abstracts hydrogen, the activation energy for the dissociation reaction leads to a value of 83.2 f 1.9 ckal/mole for D(K-CHC1CH:CHZ) at 298'K. Taking D(H-CHCICH2CHa)

= 95.2 + 1.0 kcal/mole a value of 12.0 f 2.1 kcal/mole is obtained for the resonance energy of the chloroallyl radical. This value in conjunction with resonance energies obtained in earlier work indicates that substitution of a hydrogen atom on the carbon atom adjacent to the double bond in the allyl radical leads to no significant variation in the allylic resonance rnergy.

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