Collect. Czech. Chem. Commun. 1994, 59, 2632-2640
https://doi.org/10.1135/cccc19942632

Kinetics of Reactions of 9-Isothiocyanatoacridine with Aromatic and Aliphatic Amines and Fluorescence Properties of the 1-Acridin-9-yl-3-alkyl(aryl)thioureas Obtained

Dana Mazagováa, Pavol Kristiana, Gejza Suchára, Ján Imricha and Marián Antalíkb

a Department of Organic Chemistry, P. J. Šafárik University, 041 67 Košice, Slovak Republic
b Department of Biochemistry, P. J. Šafárik University, 041 67 Košice, Slovak Republic

Abstract

Kinetics of nucleophilic addition reaction of 9-isothiocyanatoacridine with seventeen aliphatic and aromatic amines in organic solvents has been studied by the VIS spectroscopic method. 9-Isothiocyanatoacridine reacted by about two orders of magnitude faster than phenyl isothiocyanate. The reaction rates of aliphatic amines were markedly affected by steric effects. Excepting 1-acridin-9-yl-3-butylthiourea (IIIo), the products obtained exhibited weaker fluorescence than the starting 9-isothiocyanatoacridine.