Homolytic and Heterolytic C-H Bond Dissociation Energies of a-V (or Ⅵ)-Group Cation-substituted Toluenes and Acetophenones

Abstract

Abstract: Eleven α-V (or Ⅵ)-group cation-substituted toluenes (1) and acetophenones (2)were synthesized.The equilibrium acidities (PK_a) of these compounds were determined indimethyl sulfoxide solution by the "Overlapping Indicator Method" and the homolytic C-Hbond dissociation energies (BDE) were derived from a thermodynamic cycle combining PK_awith oxidation potential of carbanion.The effects of the a-positively charged groups on thethermodynamic stabilities of sixteen Ylide carbanions and the corresponding Ylide-like radi-cals and the remote structral effect have been discussed.

Key words: PK_a, Homolytic bond dissociation energy, Thermodynamic stability, Ylide, Radical

CLC Number:

O642.1

TrendMD:

CHENG Jin-Pei, LIU Bo, LU Yun, MI Jiang-Lin, HUAN Zhen-Wei. Homolytic and Heterolytic C-H Bond Dissociation Energies of a-V (or Ⅵ)-Group Cation-substituted Toluenes and Acetophenones[J]. Chem. J. Chinese Universities, 1997, 18(7): 1081.

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Homolytic and Heterolytic C-H Bond Dissociation Energies of a-V (or Ⅵ)-Group Cation-substituted Toluenes and Acetophenones

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