Synthesis of some 1,8-dioxoacridine carboxylic acid derivatives and the determination of their ionization constants in ethanol-water mixtures


Saygilu R., Ulus R., Yesildag I., İNAL E. K., KAYA M., KALFA O. M., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1083, pp.252-259, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1083
  • Publication Date: 2015
  • Doi Number: 10.1016/j.molstruc.2014.12.002
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.252-259
  • Keywords: 1,8-Dioxoacridine carboxylic acid derivatives, Ethanol-water mixtures, Ionization constants, Potentiometric titration, Solvent effect, AQUEOUS-ORGANIC SOLVENTS, PROTONATION CONSTANTS, SUBSTITUTED SALICYLIDENEANILINES, DISSOCIATION-CONSTANTS, AMINO-ACIDS, MEDIA, POLYMERIZATION, POTENTIOMETRY, SOLVATION, DYES
  • Ankara University Affiliated: Yes

Abstract

Four novel compounds of 1,8-dioxoacridine carboxylic acid derivatives (4-(3,3,6,6-tetramethyl-1,8-dioxo-9-phenyl-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzoic acid, 4-(9-(4-cyanophenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzoic acid, 4-(9-(4-hydroxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzoic acid, 4-(9-(2,4-dichlorophenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzoic acid) were prepared by the reaction of the 4-substitute benzaldehyde (hydrogen, hydroxyl, cyano, and 2,4-dichloro), 4-aminobenzoic acid, and 5,5-dimethylcyclohexane-1,3-dione in the presence of p-dodecylbenzenesulfonic acid. They were characterized by using FT-IR, H-1-NMR, C-13-NMR, GC-MS spectroscopic techniques. The stoichiometric ionization constants of these compounds were determined in ethanol-water mixtures of 50%, 60% and 70% ethanol (v/v) by potentiometric titration method and the ionization constants were calculated with three different ways. The effects of solvent composition and substituent groups on ionization constants of 1,8-dioxoacridine carboxylic acids were also discussed. (C) 2014 Elsevier B.V. All rights reserved.