Abstract: Novel naphtho- and anthraquinones conjugated with benzo- and dibenzo-18-crown-6 ethers were obtained. Their complexation reactions with Groups Ia and IIa metal perchlorates in acetonitrile were studied by spectrophotometric titration. In most cases, the complexation involves the crown ether moiety; the stability constant of the resulting complex decreases in the following order: Ba2+ > Sr2+ > Ca2+ > Na+. For crown-containing anthraquinone imines characterized by prototropic "imine-enamine" tautomerism, the complexation shifts the equilibrium toward the imine species, which allow these compounds to be classified among a rarely occurring type of tautomeric chromoionophores. Unlike other cations, the magnesium ions preferably interact with the heteroatoms of the anthraquinone moiety (the imine N atom, the OH group, and the carbonyl O atom of the benzamido group); the logK value reaches 4.4. The chelation to the Mg2+ cations and the effect of the complexation on the tautomeric equilibrium was confirmed by quantum chemical calculations.

Cite: Martyanov T.P. , Ushakov E.N. , Savelyev V.A. , Klimenko L.S.
Crown-containing naphtho- and anthraquinones: synthesis and complexation with alkali and alkaline-earth metal cations
Russian Chemical Bulletin. 2012. V.61. N12. P.2282-2294. DOI: 10.1007/s11172-012-0323-z WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Мартьянов Т.П. , Ушаков Е.Н. , Савельев В.А. , Клименко Л.С.
КРАУНСОДЕРЖАЩИЕ НАФТО- И АНТРАХИНОНЫ: СИНТЕЗ И КОМПЛЕКСООБРАЗОВАНИЕ С КАТИОНАМИ ЩЕЛОЧНЫХ И ЩЕЛОЧНОЗЕМЕЛЬНЫХ МЕТАЛЛОВ
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2012. №12. С.2261. РИНЦ

Dates:

Published print:	Dec 1, 2012
Published online:	Sep 11, 2013

Identifiers:

Web of science	WOS:000324216100012
Scopus	2-s2.0-84884266183
Elibrary	20474956
OpenAlex	W2059857359

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