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- W2334127072 endingPage "13817" @default.
- W2334127072 startingPage "13804" @default.
- W2334127072 abstract "The influence of alkene functionality on the energetics and kinetics of radical initiated thiol–ene click chemistry has been studied computationally at the CBS-QB3 level. Relative energetics (ΔH°, ΔH⧧, ΔG°, ΔG⧧) have been determined for all stationary points along the step-growth mechanism of thiol–ene reactions between methyl mercaptan and a series of 12 alkenes: propene, methyl vinyl ether, methyl allyl ether, norbornene, acrylonitrile, methyl acrylate, butadiene, methyl(vinyl)silanediamine, methyl crotonate, dimethyl fumarate, styrene, and maleimide. Electronic structure calculations reveal the underlying factors that control activation barriers for propagation and chain-transfer processes of the step-growth mechanism. Results are further extended to predict rate constants for forward and reverse propagation and chain-transfer steps (kP, k–P, kCT, k–CT) and used to model overall reaction kinetics. A relationship between alkene structure and reactivity in thiol–ene reactions is derived from the results of kinetic modeling and can be directly related to the relative energetics of stationary points obtained from electronic structure calculations. The results predict the order of reactivity of alkenes and have broad implications for the use and applications of thiol–ene click chemistry." @default.
- W2334127072 created "2016-06-24" @default.
- W2334127072 creator A5047206528 @default.
- W2334127072 creator A5059351242 @default.
- W2334127072 date "2012-08-08" @default.
- W2334127072 modified "2023-10-05" @default.
- W2334127072 title "Thiol–Ene Click Chemistry: Computational and Kinetic Analysis of the Influence of Alkene Functionality" @default.
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