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Communication | Regular issue | Vol 12, No. 5, 1979, pp.631-636
Published online, 1st January, 1970
DOI: 10.3987/R-1979-05-0631
Reaction at C-9 of Acridine Derivatives. Part XVI. Kinetics of Condensation of 9-Chloroacridine with Some Phenols

Andrzej Ledóchowski,* Antoni Kunikowski, Ewa Zylkiewicz, and Maria Drzewicka

*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 reactions of 9-chloroacridine with p-chlorophenol, phenol and p-cresol in CCl4 at 25 - 60°C was found to be approximate to the second order equation under the conditions used. The most reactive was p-chlorophenol, less phenol and even a little less p-cresol. The reaction occurs through the intermediate, i.e., a hydrogen bonded complex, 9-chloroacridine.phenol, formed in the first reversible reaction step (equations (3) and (4)). The different reactivities observed for variously substituted phenols are due to different strengths of hydrogen bonds formed by them with the acridine nucleus decreasing in this way the electron density at C-9 atom.