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• W3015508596 endingPage "2800" @default.
• W3015508596 startingPage "2793" @default.
• W3015508596 abstract "The hydrogen atom transfer reactions that underlie peroxide-initiated modifications of polyolefin architectures and ambient-temperature air oxidations are examined through a combination of experiments and quantum chemical calculations on model hydrocarbons. The regioselectivity of H-atom from pentane, 2,4-dimethylpentane, and 2,2,4,4-tetramethylpentane to t-BuO• generated from tert-butyl hyponitrite at 25 °C was quantified by trapping of the alkyl radicals with a UV-active nitroxide. The data show that hydrocarbon reactivity toward t-BuO• does follow neither well-established trends in homolytic C–H bond dissociation energy (tertiary > secondary > primary) nor trends in the susceptibility of polyolefins to autoxidation. These experiments, together with quantum chemical calculations conducted at the CBS-QB3 level of theory, reveal the importance of entropic effects in these exergonic H-atom transfer processes. In contrast, the endergonic nature of H-atom abstraction by t-BuOO• produces conventional hydrocarbon reactivity patterns, as enthalpic contributions to transition-state energies are dominant. These findings bring clarity to the structure/reactivity relationships of polyolefins in the field of radical chemistry." @default.
• W3015508596 created "2020-04-17" @default.
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• W3015508596 date "2020-04-08" @default.
• W3015508596 modified "2023-10-14" @default.
• W3015508596 title "Hydrogen Atom Abstraction from Polyolefins: Experimental and Computational Studies of Model Systems" @default.
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• W3015508596 doi "https://doi.org/10.1021/acs.macromol.9b02091" @default.
• W3015508596 hasPublicationYear "2020" @default.
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