Chemoselectivity

Chemoselectivity is the preferential reaction of a chemical reagent with one of two or more different functional groups.[1]

In a chemoselective system, a reagent in the presence of an aldehyde and an ester would mostly target the aldehyde, even if it has the option to react with the ester. Chemoselectivity is an area of interest in chemistry because scientists want to recreate complex biological compounds, such as natural products, and make specific modifications to them.[2]

Most chemical reactions bring together atoms that have negative charge character and atoms that have positive charge character.[3] When evaluating possible reaction outcomes, several factors should be considered. The most important being identifying where in the molecule has the most electron density and where has the least.[3] This analysis gives a good prediction of reactivity, but more factors such as connectivity, atomic orbital overlap, solvent effects, and the addition of supporting reagents can affect the reaction outcome.  

  1. ^ "Chemoselectivity (chemoselective)". IUPAC Compendium of Chemical Terminology (3rd ed.). International Union of Pure and Applied Chemistry. 2006. doi:10.1351/goldbook.C01051 – via Online version 3.0.1, 2019.
  2. ^ Shenvi, Ryan A.; O’Malley, Daniel P.; Baran, Phil S. (2009-04-21). "Chemoselectivity: The Mother of Invention in Total Synthesis". Accounts of Chemical Research. 42 (4): 530–541. doi:10.1021/ar800182r. ISSN 0001-4842. PMC 2765532. PMID 19182997.
  3. ^ a b Zumdahl, Steven S. (1995). Chemical Principles (2nd ed.). Lexinton, MA, USA: HEATH. ISBN 0669393215.