Crown-containing naphtho- and anthraquinones: synthesis and complexation with alkali and alkaline-earth metal cations Full article
| Journal |
Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
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| Output data | Year: 2012, Volume: 61, Number: 12, Pages: 2282-2294 Pages count : DOI: 10.1007/s11172-012-0323-z | ||||||
| Tags | naphthoquinone; anthraquinone; crown ether; chromoionophore; prototropic tautomerism; complexation; parameterized matrix modeling; spectrophotometric titration | ||||||
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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 OpenAlex
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 OpenAlex
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
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 |