Influence of cetophenolic and diphenolic intramolecular hydrogen bonding on the chromatographic and spectroscopic properties of hydroxyanthraquinones

Autor:	Paul Archier, Catherine Vieillescazes, Michael Hovaneissian
Rok vydání:	2007
Předmět:	Chromatography Molecular model Hydrogen bond Process Chemistry and Technology General Chemical Engineering Alizarin Photochemistry Anthraquinone chemistry.chemical_compound chemistry Absorption band Intramolecular force Bathochromic shift Spectroscopy
Zdroj:	Dyes and Pigments. 74:706-712
ISSN:	0143-7208
DOI:	10.1016/j.dyepig.2006.05.003
Popis:	Anthraquinones have been widely employed for dyeing textiles in combination with various mordants. Many papers have dealt with the modification of optical properties induced by the formation of dye complexes under various pH conditions. This paper deals with the characterization of diphenolic intramolecular hydrogen bonding via molecular modeling and cetophenolic interactions by FT-IR spectroscopy to determine their effect on the spectroscopic and chromatographic properties of hydroxyanthraquinones (anthraflavic acid, alizarin, quinizarin and purpurin). The formation of cetophenolic hydrogen bonding induces a substantial bathochromic shift to the visible absorption band. Moreover, it implies that the constitution of hypercyclised aromatic systems is potentially responsible for the fluorescence of quinizarin and purpurin. This study also demonstrates the modification of the chromatographic retention of dihydroxyanthraquinones on apolar stationary phase consequent to the monopolization of polar groups involved in the formation of such interactions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dc6c8417ca96158ad470911c20d12f92 https://doi.org/10.1016/j.dyepig.2006.05.003 Zobrazit plný text záznamu Full Text from ScienceDirect