Document Type
Article
Rights
This item is available under a Creative Commons License for non-commercial use only
Disciplines
1.4 CHEMICAL SCIENCES
Abstract
A simple analytical LC-MS (Liquid Chromatography Mass Spectrometry) method and associated instrumentation has been adapted for use by the organic chemist to yield mg quantities of target compound from a reaction mixture. Calix[4]arene 3 was identified as representing 51% of total peak area of a reaction mixture containing no less than 10 components, using LC-MS. This peak corresponded to a mass of 878.8, equivalent to a complex of 3 and an ammonium cation. Molecular models further rationalise this observation by showing that the asymmetric binding cavity of 3 is suitable for binding tetrahedral guests like the ammonium ion. By scaling up the LC method, using analytical instrumentation, 55mg of 98% pure 3 were isolated with a recovery yield of 90% in 1 hr. The current method represents a powerful and easily adapted tool for monitoring a challenging synthesis which combines identification, efficient separation and partial characterisation for reaction mixture components using readily available instrumentation and methods.
DOI
http://doi.org10.1080/10610270500138789
Recommended Citation
Schazmann, B.(2005) Identification and recovery of an asymmetric calix[4]arene tetranitrile derivative using liquid chromatography and mass spectrometry. Supramolecular Chemistry, 2005, 17, 393-399. DOI:10.1080/10610270500138789
Funder
Enterprise Ireland, grant code SC/2002/161, Science Foundation Ireland support under the Adaptive Information Cluster award (SFI03/IN3/1361)
Publication Details
Supramolecular Chemistry