Spectroscopic and spectrometric studies of anion recognition with calix[4]pyrroles in different reaction conditions.
The binding studies of calix[4]pyrroles (1-6) with fluoro, chloro, bromo, iodo and sulphato anions generated from normal-tetrabutylammoniumfluoride, normal-tetrabutylammoniumchloride, normal-tetrabutylammoniumbromide, normal-tetrabutylammoniumiodide, and normal-tetrabutylammoniumsulphate respectively were investigated by electrospray ionization mass spectrometry (ESI-MS) in dichloromethane-acetonitrile in negative ion mode. The efficacy of a particular calix[4]pyrrole to bind with anions was found maximum at low cone voltage of the instrument, at high cone voltage the binding was suppressed due to removal of anion from the cavity of the macrocycles. The binding strength was found inversely proportional to the size of anion for a particular calix[4]pyrrole. The fragmentation pattern of calix[4]pyrrole was observed at higher cone voltage of ESI-MS and was interpreted. The association constants of calix[4]pyrroles and anions obtained from electronic transition studies were in good agreement with that observed from (1)H NMR titration studies.
Giri
Nand Gopal
NG
Department of Chemistry, Bio-organic Research Laboratory, University of Delhi, Delhi 110 007, India.
Chauhan
Shive Murat Singh
SM
D000838:Anions / Q000737:chemistry / Q000378:metabolism*; D047250:Calixarenes / Q000737:chemistry*; D002384:Catalysis; D005456:Fluorescent Dyes / Q000737:chemistry; D008954:Models, Biological; D011166:Porphyrins / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013057:Spectrum Analysis / Q000379:methods
D000838:Anions; D005456:Fluorescent Dyes; D011166:Porphyrins; C469811:calix(4)pyrrole; D047250:Calixarenes