ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Reduction of 1-nitro-1-(5-nitro-2-furyl)-2-(substituted phenyl)ethylenes on mercury electrode

J. Černák, A. Staško, F. Tomanovič, L. Némethy, and I. Sroková

Department of Analytical Chemistry, Slovak Technical University, CS-812 37 Bratislava

Abstract:  1 -Nitro-l-(5-nitro-2-furyl)-2-(substituted phenyl)ethylenes in dichloromethane solutions are reduced on the dropping mercury electrode in two or three one-electron steps (E_1/2¹=-0.6V, E_1/2²=-1.25 V, and E_1l2³=-1.4V against 1 M-LiCl, Hg₂Cl₂ /Hg electrode). In the reduction, instable radicals with lifetime of a few seconds and with centre of the unpaired electron on the nitro group (e.s.r. investigation) are formed. E_1/2 and splitting constants of the nitrogen nucleus a_N correlate satisfactorily with the Hammett constants ox of substituents on the benzene ring (E_1/2¹=-0.704 + 0.347 σ_o,p and a_N⁵ = 0.678-0.0339 σ_o,p).

Full paper in Portable Document Format: 373a385.pdf

Chemical Papers 37 (3) 385–394 (1983)