Journal of the Chemical Society. Perkin transactions II p. 277 - 284 (1986)
Update date:2022-08-11
Topics:
Alder, Roger W.
Bonifacic, Marija
Asmus, Klaus-Dieter
Absolute rate constants have been measured for the reaction of the N<*>N three-electron bonded 1,6-diazabicyclo<4.4.4>dodecane radical cation (<4.4.4>+.) with various free radicals produced by means of pulse radiolysis.Reduction and oxidation reactions occur with rate constants generally somewhat below the diffusion limit.This is considered to reflect the inwardly oriented structure of the <4.4.4>+..High rate constants (ca. 1E9 mol-1 dm3 s-1) have been measured for hydrogen-atom abstraction from <4.4.4>+. by almost all radicals except eeq-.The most remarkable of these reactions appears to be H-atom abstraction by a thiyl radical <(CH3)3CS.>, which occurs with k 3.2E9 mol-1 dm3 s-1.This indicates highly labile C-H bonds in <4.4.4>+., which are considered to be those located on CH2 groups α to the nitrogen atoms.The fast radical-radical H-atom transfer is considered to be energetically assisted by favourable stereoelectronics and least heavy atom motion.
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