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Abstrakt
The preparation and characterization of products of the chemical and photochemical rearrangements of a 19-membered o,o'-azoxybenzocrown were presented. In photochemical rearrangement, besides expected product i.e. 19-membered o-hydroxy-o,o'-azobenzocrown (19-o-OH), obtained under defined conditions with 75% yield, also other macrocyclic products were isolated and identified, namely: 19-membered p-hydroxy-o,o'-azobenzocrown (19-p-OH), 21-membered o'-hydroxy-o,p'-azobenzocrown (21-o'-OH) and 19-membered macrocycle containing 5-membered ring bearing an aldehyde group (19-al). The structures of two atypical products of the photochemical rearrangement - 21-o'-OH and 19-al - were determined in the solid state by the X-ray method and in solution using NMR spectroscopy. Tautomeric equilibrium of the formed hydroxyazobenzocrowns and its change depending on acidity/basicity of the environment and alkali and alkaline earth metal cations complexation were studied using UV-Vis spectrophotometry, spectrofluorimetry and 1H NMR spectroscopy.
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- Wersja publikacji
- Accepted albo Published Version
- Licencja
- Copyright (2020 Wiley-VCH GmbH)
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Informacje szczegółowe
- Kategoria:
- Publikacja w czasopiśmie
- Typ:
- artykuły w czasopismach
- Opublikowano w:
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ChemPlusChem
nr 85,
strony 2067 - 2083,
ISSN: 2192-6506 - Język:
- angielski
- Rok wydania:
- 2020
- Opis bibliograficzny:
- Wagner-Wysiecka E., Szulc P., Luboch E., Chojnacki J., Szwarc-Karabyka K., Łukasik N., Murawski M., Kosno M.: Photochemical Rearrangement of a 19-Membered Azoxybenzocrown: Products and their Properties// ChemPlusChem -Vol. 85,iss. 9 (2020), s.2067-2083
- DOI:
- Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1002/cplu.202000474
- Weryfikacja:
- Politechnika Gdańska
wyświetlono 193 razy