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The barriers of both FSA- and BSA-paths increase with incremental solvation, whereas the change of XTS depends on the type of nucleophile. When Y = HO/F, the order of the barriers is BSA less then XC less then FSA for n = 0-2, and the order inverts to XC less then BSA less then FSA for n = 1 (Y = Br/I) and n = 2 (Y = Cl/Br/I), where the latter suggests an increasing participation of the halogen-bonded complex in the SN2 reactions. Comprehensive analyses on the structure, charge distribution, and energetics of XC and XTS are provided. This w
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