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Variations in rotational barriers of allyl and benzyl cations, anions, and radicals

Li, Zhe ; Bally, Thomas ; Houk, Kendall N. ; Borden, and Weston Thatcher

In: The Journal of Organic Chemistry, 2016, vol. 81, no. 20, p. 9576–9584

High accuracy quantum chemical calculations show that the barriers to rotation of a CH2 group in the allyl cation, radical, and anion are 33, 14, and 21 kcal/mol, respectively. The benzyl cation, radical, and anion have barriers of 45, 11, and 24 kcal/mol, respectively. These barrier heights are related to the magnitude of the delocalization stabilization of each fully conjugated system. This...