The Effect of a Cyano Group on the Thermodynamic Ease of Electron Removal from Hydrazines

Article abstract of DOI:10.1021/jo00171a013

Formal oxidation potentials relative to SCE are reported for several cyano-substituted hydrazines and their analogues with the cyano group replaced by a methyl group. ΔE*'was 0.83 V for 2-cyano- and 2-methyl-3-tert-butyl-2,3-diazabicycloheptane (1(CN) and 1(Me)), 0.35 V for trimethyl(cyanomethyl)hydrazine and ethyltrimethylhydrazine (3(CN) and 3(Me)), and 0.23 V for (β-cyanoethyl)trimethylhydrazine and propyltrimethylhydrazine (4(CN) and 4(Me)).The ESR spectrum of 1(CN)-d₂ has nitrogen splittings of 17.2 and 7.7 G.The significance of these results is discussed.