Spectrophotometric and x-ray crystallographic studies of 1-carbamoylbenz-[c,d]indol-2-ones

Autor: Kuz'mina, L. G., Struchkov, Yu. T., Grigor'eva, L. P., Ezhkova, Z. I., Zaitsev, B. E., Trunov, S. P., Vasil'eva, N. I., Dyumaev, K. M.
Zdroj: Chemistry of Heterocyclic Compounds; August 1984, Vol. 20 Issue: 8 p906-910, 5p
Abstrakt: On the basis of a measurement of the frequencies and intensities of the stretching vibrations of the amino, amido, and ester groups in the IR spectra, it was established that products of the reaction of N-benzenesulfonylhydroxynaphthalimides with ammonia in alcohol solutipns have a structure of the type of 1-carbamoylbenz[c,d]-indol-2-ones and are not molecules with a seven-membered heterocycle, by analogy with 3-oxido-2-alkylnaphtho[1,8-d,e][1,3] oxoniazepin-1-ones. A determination of the molecular and crystal structure of one of these compounds (C13H10N2O2) confirmed this conclusion: The molecule is 1-(N-methylcarbamoyl)benz[c,d]indol-2-one. In the naphthalene ring of the molecule the bond angles at the central bond are deformed analogously to that found in acenaphthene. The intramolecular hydrogen bond O···HN closes a six-membered ring in the molecule. The crystal is constructed from dimers formed by intermolecular hydrogen bonds O···HN.
Databáze: Supplemental Index