Abstract
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-(α-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 theα-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 theσ-π approximation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
R. Hinman and E. Whipple, J. Am. Chem. Soc.,84, 2534 (1962).
L. G. Yudin, V. A. Budylin, A. N. Kost, and V. I. Minkin, Dokl. Akad. Nauk SSSR,176, 1096 (1967).
N. A. Kogan, Reakts. Sposobn. Org. Soedin., No. 3, 655 (1975).
M. J. S. Dewar, Molecular Orbital Theory of Organic Chemistry, McGraw-Hill (1969).
N. Mataga and K. Nishimoto, Z. Phys. Chem.,136, 140 (1957).
V. N. Rusinova, Yu. I. Smushkevich, T. A. Kozik, and N. N. Suvorov, Zh. Org. Khim.,8, 1735 (1972).
N. A. Kogan, Khim. Geterotsikl. Soedin., No. 6, 857 (1975).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 60–62, January, 1978.
Rights and permissions
About this article
Cite this article
Kogan, N.A., Kul'bitskii, G.N. Structure of indolylphenylmethyl cations. Chem Heterocycl Compd 14, 46–48 (1978). https://doi.org/10.1007/BF00635941
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00635941