ortho-Substituted (aryl)(3-nitrobenzo[b]thiophen-2-yl)amines: study of the electrochemical behavior.
The reduction potentials of the title compounds 4 have been measured by cyclic voltammetry. The effect of the substituents has been evaluated by using a linear free energy relationship treatment, thus evidencing that the present ortho-substituents affect the Epc values basically by electronic effects. A comparison with data previously collected on ortho-substituted (aryl)(2-nitrobenzo[b]thiophen-3-yl)amines 3 has provided some interesting information. Different electrochemical behaviors are observed during the reduction (a reversible process and an irreversible process are operating in 3 and 4, respectively): to elucidate the reasons for this different behavior, the "reversible" reduction potentials of 5 and of 6 have been measured. Moreover, higher susceptibility constants have been calculated for compounds of series 4 with respect to those of series 3 (rho4 = 329 and rho3 = 182, respectively). A rationale for all of these findings has been offered.
Cosimelli
Barbara
B
Dipartimento di Chimica Farmaceutica e Tossicologica, Università degli Studi di Napoli Federico II, Via Montesano 49, 80131 Napoli, Italy.
Lanza
Camilla Zaira
CZ
Scavetta
Erika
E
Severi
Elda
E
Spinelli
Domenico
D
Stenta
Marco
M
Tonelli
Domenica
D
D000588:Amines / Q000737:chemistry*; D004563:Electrochemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines