Electrochemical oxidation of calixarenes: stabilisation by intramolecular π–π interactions of electrogenerated phenoxylium cations

Autor:	Rame Vataj, Dominique Matt, Catherine Jeunesse, Alain Louati
Rok vydání:	2004
Předmět:	General Chemical Engineering chemistry.chemical_element Electrochemistry Photochemistry Medicinal chemistry Analytical Chemistry chemistry.chemical_compound Electron transfer chemistry Nucleophile Intramolecular force Calixarene Cyclic voltammetry Platinum Dichloromethane
Zdroj:	Journal of Electroanalytical Chemistry. 565:295-299
ISSN:	1572-6657
DOI:	10.1016/j.jelechem.2003.10.022
Popis:	5,11,17,23- Tetra-tert -butyl-25,27-bis( p -toluenesulfonyl)-26,28-bis(hydroxy)calix[4]arene ( 3 ) has been prepared from p - tert -butylcalix[4]arene and p -toluenesulfonyl chloride. The oxidative electrochemistry of 3 was studied in dichloromethane solution at a platinum electrode. As shown by detailed voltammetric, coulometric and spectroelectrochemical experiments the hydroxyl groups of 3 behave as non interacting sites, each hydroxyl group undergoing an irreversible two-electron transfer governed by an ECE mechanism to form the corresponding phenoxylium cation. The resulting di-(phenoxylium cation) [ 3 -2H] 2+ 4 was found to be stable for at least 2 h in dichloromethane. Nucleophilic attack of residual water on 4 ultimately led to the corresponding calix[4]diquinone 5 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::64a45737848678e6ba550ce5a60d5b78 https://doi.org/10.1016/j.jelechem.2003.10.022 Zobrazit plný text záznamu Full Text from ScienceDirect