The Polarographic Behavior of Isatin. II. Behavior of Isatin and N-Alkylisatins in Ethanol Solutions

Abstract

Studies of the polarographic behavior of isatin solutions have been extended to cover the behavior of isatin and N-alkylisatins in solution in 50% ethanol. A rationalization of the behavior of these compounds has been suggested.

Substituent and solvent dependence of the one-electron reduction of 5-substituted-N-methylisatins in aprotic solvents

“…Since many isatin-based organic syntheses utilize nonpolar solvents, an understanding of isatin redox properties in organic solvents becomes particularly important. Electrochemical data for isatins is sparse, with few potentials available for the reduction of isatins and their derivatives in protic and aprotic solvents [9][10][11][12].…”

Aromatic and heterocyclic semidiones

“…Isatin is capable of forming a relatively stable purple enolate anion in nonaqueous basic solutions (8) and this gauss. The decrease of the nitrogen splitting and increase of the aromatic ring proton splittings in the dianion radical relative to the anion radical indicates the re pulsive effect of a high heteroatom charge density on the unpaired electron density.…”

“…Of the compounds to be discussed in this thesis the only extensive previous studies of reduction potentials were of isatin and the substituted isatins (7,8). These studies were performed in aqueous solution primarily for comparison with aqueous biological dehydrogenation reactions (j).…”

Aromatic and heterocyclic semidiones

“…The dicarbonyl moiety in benzoquinones is only a part of the entire potential aromatic system, which is the actual Of the compounds to be discussed in this thesis the only extensive previous studies of reduction potentials were of isatin and the substituted isatins (7,8). These studies were performed in aqueous solution primarily for comparison with aqueous biological dehydrogenation reactions (j).…”