Transition-state polarization in cleavage of carbon-carbon bonds in radical anions

P Maslak, JN Narvaez, J Kula…

Index: Maslak, Przemyslaw; Narvaez, Javier N.; Kula, Jozef; Malinski, David S. Journal of Organic Chemistry, 1990 ,  vol. 55,  # 15  p. 4550 - 4559

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Citation Number: 20

Abstract

The substituent effect on the rate of CC bond cleavage in radical anions of 1-(4-nitrophenyl)- 2-(substituted-phenyl)-1, 1, 2, 2-tetraethylethanes has been explored. The data provide evidence for two distinctive modes of bond scission. One mode is characterized by a significant negative charge transfer across the scissile bond in the transition state. Such polarization of the transition state is in contradiction to the prediction based on the ...