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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 (E1/21=-0.6V, E1/22=-1.25 V, and E1l23=-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. E1/2 and splitting constants of the nitrogen nucleus aN correlate satisfactorily with the Hammett constants ox of substituents on the benzene ring (E1/21=-0.704 + 0.347 σo,p and aN5 = 0.678-0.0339 σo,p).

Full paper in Portable Document Format: 373a385.pdf


Chemical Papers 37 (3) 385–394 (1983)

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