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The bond dissociation energy of the C–H bond at the α-position of an ether oxygen in cyclopentyl methyl ether (CPME) has been evaluated theoretically to be 393.3 kJ/mol by using an isodesmic reaction method. Essential factors accounting for this rather higher bond dissociation energy in CPME comparable to secondary C–H bond have been investigated on the basis of the structures and their thermodynamic data such as heats of formation (ΔHf°) of CPME radical and relevant ether radicals evaluated by the theoretical approach.
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Hoshino et al. (2008) studied this question.
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