High throughput physical organic chemistry: analytical constructs for monomer reactivity profiling.
A polymer-supported analytical construct was used to quantify the reactivity of a range of monomers in the Ugi four-component condensation using positive electrospray ionization mass spectrometry (MS) as a quantitative analytical tool. The construct incorporated a bromo group to act as a peak splitter and a quaternary ammonium to act as a MS sensitizer and ionization leveler, thereby allowing direct quantitation of the cleaved adducts by MS. The relative reactivities of 10 carboxylic acids were quantified by the relative levels of product generated as determined by MS and 10 isonitriles, and 10 aldehydes were investigated in the same way. The effect of concentration variations on monomers reactivity and product profiles were rapidly determined using this approach, and the method opens up the way for studying, in a single pot, multiple reactions with a broad range of monomers under identical and self-consistent reaction conditions.
Portal
Christophe
C
Combinatorial Centre of Excellence, School of Chemistry, The University of Edinburgh, Edinburgh EH9 3JJ, UK.
Launay
Delphine
D
Merritt
Andrew
A
Bradley
Mark
M
D000447:Aldehydes / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D020650:Combinatorial Chemistry Techniques; D013058:Mass Spectrometry; D009570:Nitriles / Q000737:chemistry; D010455:Peptides; D021241:Spectrometry, Mass, Electrospray Ionization
D000447:Aldehydes; D002264:Carboxylic Acids; D009570:Nitriles; D010455:Peptides