Structure of indolylphenylmethyl cations

Autor: Kogan, N. A., Kul'bitskii, G. N.
Zdroj: Chemistry of Heterocyclic Compounds; January 1978, Vol. 14 Issue: 1 p46-48, 3p
Abstrakt: The charge distribution in 1-methyl-2-carboxy-3-indolylphenylmethyl cation (II), which is formed by dissociation of the C-X bond in 1-methyl-2-carboxy-3-(a-X-benzyl)indoles (I) in H2SO4 solution, was studied by PMR and13C NMR spectroscopy. Cation II may have a structure with a positive charge on the benzyl carbon atom (IIa), the nitrogen atom (IIc), or on thea-carbon atom of the indole ring (IIc). Structures IIc and IIa make the major contributions to the II structure; this is confirmed by calculations by the Pariser-Parr-Pople (PPP) method within thes-p approximation.
Databáze: Supplemental Index