The Mechanism of Formation and Lifetimes of Halogenated Ketenes Page: 4
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It was found, for these ketenes, that the rate of decrease
of the ketene absorption in the infrared followed closely
a second order rate law. This suggested that "dimeriza-
tion" may be the initial pathway, followed by polymeriza-
tion for halogenated ketene decay.
The results of the investigation into the mechanism of
dehydrohalogenation and ketene lifetime were complemented
by CNDO/2 calculations of the acid halides and ketenes
studied. It was concluded that the mechanism of dehydro-
halogenation of acid halides involves a complex series of
equilibria,and it has become increasingly apparent that
halogenated ketenes are produced through the acylammonium
salt. The enolate salt appears to be a dead end in the
reaction to form ketenes. It was also demonstrated that
increasing steric bulk has a stabilizing effect on ketene
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Scherubel, Gary. The Mechanism of Formation and Lifetimes of Halogenated Ketenes, thesis, August 1974; Denton, Texas. (digital.library.unt.edu/ark:/67531/metadc500555/m1/4/: accessed January 23, 2019), University of North Texas Libraries, Digital Library, digital.library.unt.edu; .