I. Covaci, T. Constantinescu, M. Cǎproiu
Nov 1, 2000
Citations
0
Influential Citations
2
Citations
Journal
European Journal of Organic Chemistry
Abstract
Reactions of substituted N-methoxynitroaniline derivatives (1) or 2-methoxyamino-3,5-dinitropyridine (2) with potassium hydroxide afford the corresponding potassium salts (K+A−) in high yield. After dissolution of these salts in dichloromethane in the presence of 18-crown-6 ether (18-C-6), the addition of petroleum ether led to the precipitation of the corresponding solid supramolecular complexes of the type [18-C-6···K]+A−, having the stoichiometry 1:1:1. The UV/vis and 1H NMR spectra are discussed. A barrier of ΔG≠ = 15.3 ± 0.2 kcal/mol for rotation about the Ar−N bond has been determined for N-methoxy-2-cyano-4,6-dinitroaniline. The supramolecular complex [18-C-6···K]+A− derived from 2 has been N-methylated with methyl iodide to afford 3, and N-arylated with 2-chloro-3,5-dinitropyridine to afford 4. The conformations of compounds 3 and 4 have been calculated.