Electrochemical study, on mercury, of a Meta-nitroarylamine derivative of nor-β-lapachone, an antitumor and trypanocidal compound

• Autor(a) principal: Souza,Antonio A. de
• Data de Publicação: 2010
• Outros Autores: Moura,Maria Aline B. F. de, Abreu,Fabiane C. de, Goulart,Marília O. F., Silva Jr.,Eufrânio N. da, Pinto,Antonio V., Ferreira,Vitor F., Moscoso,Raúl, Núñez-Vergara,Luis J., Squella,Juan A.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Química Nova (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422010001000013
• topic: nitroquinones; semiquinone stability; kinetic constants

The electrochemistry of 2,2-dimethyl-(3H)-3-(N-3'-nitrophenylamino)naphtho[1,2- b]furan-4,5-dione ([Q]-PhNO2), on mercury was investigated. The first peak is consistent with a quasi-reversible one-electron reduction of the ortho-quinone, forming [Q•-]-PhNO2, while the second one, bielectronic, corresponds to the simultaneous reduction of the latter radical to a dianion and the nitro group to a nitro radical anion. The second order rate constant, k disp, for the decay of [Q•-]-PhNO2 is 15.188 x 10³ ± 827 mol"1 L s"1 and the t1/2 equals 0.06 s. E¹7Ic values for [Q]-PhNO2 and its precursor, nor-β-lapachone, are similar. The ease of semiquinone generation and its stability are parameters statistically relevant in the correlation biochemical/theoretical aspects.