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Communication | Regular issue | Vol 9, No. 10, 1978, pp.1335-1344
Published online, 1st January, 1970
DOI: 10.3987/R-1978-10-1335
Reactions at C-9 Position of Acridine Derivatives. Part XVIII. On the Mechanism of Hydrolysis (Solvolysis) of 9-Chloroacridine in Aqueous Acetic Acid

Stanislaw Skonieczny*

*Laboratory of Chemistry and Biochemistry of Antitumour Compound, Institute of Organic and Food Chemistry and Technology, Techinical University of Gdansk, 80-952 Gdansk 6, Poland

Abstract

The kinetics of solvolysis of 9-chloroacridine (1) in 80 % aqueous acetic acid and its hydrolysis in aqueous hydrochloric acid of pH from 0 to 3 have been studied. The reaction occurs in two distinct stages in acetic acid but follows pseudo-first-order kinetics with respect to 1 in hydrochloric acid. No traces of the Π-complex (2) suggested for the former case are observed in the u.v. spectra, and reaction rate constant for the hydrolysis in hydrochloric acid are identical with those of the second step of the consecutive reaction in acetic acid at the same concentration of 1. This implies a mechanism with 9-chloroacridine hydrochloride (5) as an intermediate in the solvolysis process. Hydrogen bonded compound 4 is discussed as a possible intermediate in most nucleophilic substitution reactions at 9-position of 1.