Acidic properties and structure of pyrrolanthrones

Autor: Kazankov, M. V., Sadovykh, E. G., Korolev, B. A.
Zdroj: Chemistry of Heterocyclic Compounds; December 1979, Vol. 15 Issue: 12 p1334-1337, 4p
Abstrakt: The NH acidity of pyrrolanthrone in dimethyl sulfoxide and the COOH acidity of pyrrolanthrone-1-carboxylic acid exceed the acidities of indole and indole-2-carboxylic acid by 6 and 2.5 orders of magnitude, respectively; this is due to the electron-acceptor effect of the condensed anthrone ring. A quantitative estimate of the effect of substituents in the 1 position on the NH acidity indicates that the bonds in the pyrrole fragment are localized to a significant degree; the C1-N bond approaches a single bond, and the C1-C10b bond consequently approaches a double bond. The effect on the NH acidity of NO2 and NH2 groups located in the anthrone fragment (in the 5 position) is examined.
Databáze: Supplemental Index