37449-71-1Relevant academic research and scientific papers
Effect of Substituents on the Bond Strength of Air-Stable Dicyanomethyl Radical Thermochromes
Peterson, Joshua P.,Geraskina, Margarita R.,Zhang, Rui,Winter, Arthur H.
, p. 6497 - 6501 (2017/06/23)
A series of substituted aryl dicyanomethyl radicals were synthesized, and the bonding thermodynamic parameters for self-dimerization were determined from van't Hoff plots obtained from variable-temperature electron paramagnetic resonance and ultraviolet-v
Resonanzstabilisierung von Alkylradikalen durch zwei geminale Cyangruppen
Pakusch, Joachim,Beckhaus, Hans-Dieter,Ruechardt, Christoph
, p. 1191 - 1198 (2007/10/02)
Effects of Substituents on the Strength of C-C bonds, 10. - Resonance Stabilization of Alkyl Radicals by Two Geminal Cyano groups The activation parameters of the homolytic cleavage of the Cq-Cq bonds of several dialkylated malonodinitriles (2-5) and of 1,1,2,2-tetracyanoethane (7) and the heat of dissociation of 6 in solution have been determined.Together with the ground state strain of the radical precursor (obtained from the heats of combustion or EFF calculations) the steric influence on the dissociation process has been determined.The resonancestabilization energy of α,α'-dicyanoalkyl radicals then calculated was (12.4 +/- 0.9) kcal/mol.This result is discussed within the concept of capto-dative stabilization.The destabilizing interaction of two geminal cyano groups is apparently the same in the ground state of 2-7 and the radicals generated from them.
