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.
^"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.
^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.
^ abZumdahl, Steven S. (1995). Chemical Principles (2nd ed.). Lexinton, MA, USA: HEATH. ISBN 0669393215.
Chemoselectivity is the preferential reaction of a chemical reagent with one of two or more different functional groups. In a chemoselective system, a...
couple with chlorinated arenes. This low reactivity is the basis for chemoselectivity for nickel insertion into the C–Br bond of bromochlorobenzene using...
variations of the Grignard reagent have been discovered to improve the chemoselectivity of the Grignard reaction, which include but are not limited to: Turbo-Grignards...
(1936). http://www.orgsynth.org/orgsyn/prep.asp?prep=cv2p0108 Link Chemoselective Nitration of Phenols with tert-Butyl Nitrite in Solution and on Solid...
considerations to be made when designing a reductive amination reaction. Chemoselectivity issues may arise since the carbonyl group is also reducible. The reaction...
therefore distinguish between very similar substrate molecules to be chemoselective, regioselective and stereospecific. Some of the enzymes showing the...
aromatic ring to give acetyl aromatic esters instead of methyl benzoates. Chemoselectivity Cryptoregiochemistry Enantioselectivity Keto–enol tautomerism Stereoselectivity...
stoichiometric amount of sodium chlorite. TEMPO oxidations also exhibit chemoselectivity, being inert towards secondary alcohols, but the reagent will convert...
Since sodium cyanoborohydride is a mild reducing agent, it gives good chemoselectivity for reaction with certain functional groups in the presence of others...
pub2. ISBN 978-3527306732. McGrath, N. A.; Raines, R. T. (2011). "Chemoselectivity in chemical biology: Acyl transfer reactions with sulfur and selenium"...
molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep...
in biology Reactivity–selectivity principle, in general chemistry Chemoselectivity, a term used in organic chemistry to describe reactivity of one functional...
substrates. Typically enzymes display three major types of selectivity: Chemoselectivity: Since the purpose of an enzyme is to act on a single type of functional...
Akula, Venugopal (2021-09-05). "Influence of Brønsted acid sites on chemoselective synthesis of pyrrolidones over H-ZSM-5 supported copper catalyst". Applied...
J. S. Dileep; Ho, ManKit M.; Toyokuni, Tatsushi (2001). "Simple and chemoselective reduction of aromatic nitro compounds to aromatic amines: reduction...
N-Dimethyl(chloromethylene)ammonium chloride [ClHC\dN+(CH3)2]Cl−) is a highly chemoselective agent for carboxylic acid reduction. It selectively activates the carboxylic...
molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction, facilitating multistep organic synthesis...
situ from NaBH4 and CeCl3(H2O)7. The Luche reduction can be conducted chemoselectively toward ketone in the presence of aldehydes or towards α,β-unsaturated...
acid–base theory Acid dissociation constants Lewis acids and bases Chemoselectivity Molecular structure Aromaticity Chemical bonding Covalent bonding Lewis...
relatively simple to synthesize. The reaction is not, however, entirely chemoselective. Strained cyclooctenes and other activated alkenes react with tetrazines...
analysis of carbonyl metabolites in human urine and fecal samples using chemoselective modification". The Analyst. 145 (11): 3822–3831. Bibcode:2020Ana...145...
acyl shift) amide-forming step under the reaction conditions used. Chemoselectivity of NCL : No side-products are formed from reaction with the other functional...
interest are DNA ligases. These molecules have demonstrated remarkable chemoselectivity in RNA branching reactions. Although each repeating unit in a RNA strand...
Sarah B.; Italia, James S.; Chatterjee, Abhishek (2017-08-30). "A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation"...
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