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Cyclic vs. acyclic allylic hydrogen abstraction: An entropy motivated process?

✍ Scribed by Gadi Rothenberg; Yoel Sasson


Book ID
104208541
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
261 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis


Optimized geometries for the reactants, products, and transition structures of cyclic and acyclic allylic hydrogen abstractions by tert-butoxy radicals were obtained by semiempirical methods. In the four model cases studied the transition structures were all early and linear, with large imaginary frequencies, around 2000 cm -*. Enthalpic effects, rather than entropic ones, are deemed as responsible for the "cyclic activation" of allylic hydrogens towards free-radicals.