In chemistry, a leaving group is defined by the IUPAC as an atom or group of atoms that detaches from the main or residual part of a substrate during a reaction or elementary step of a reaction. However, in common usage, the term is often limited to a fragment that departs with a pair of electrons in heterolytic bond cleavage. In this usage, a leaving group is a less formal but more commonly used synonym of the term nucleofuge. In this context, leaving groups are generally anions or neutral species, departing from neutral or cationic substrates, respectively, though in rare cases, cations leaving from a dicationic substrate are also known.
A species' ability to serve as a leaving group depends on its ability to stabilize the additional electron density that results from bond heterolysis. Common anionic leaving groups are halides such as and , and sulfonate esters such as tosylate (), while water (), alcohols (), and amines () are common neutral leaving groups.
In the broader IUPAC definition, the term also includes groups that depart without an electron pair in a heterolytic cleavage (groups specifically known as an electrofuges), like or , which commonly depart in electrophilic aromatic substitution reactions. Similarly, species of high thermodynamic stability like nitrogen () or carbon dioxide () commonly act as leaving groups in homolytic bond cleavage reactions of radical species. A relatively uncommon term that serves as the antonym of leaving group is entering group (i.e., a species that reacts with and forms a bond with a substrate or a substrate-derived intermediate).
In this article, the discussions below mainly pertain to leaving groups that act as nucleofuges.
The physical manifestation of leaving group ability is the rate at which a reaction takes place. Good leaving groups give fast reactions. By transition state theory, this implies that reactions involving good leaving groups have low activation barriers leading to relatively stable transition states.
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Acquisition des notions fondamentales liées à la réactivité des molécules organiques, identification de la structure de petites molécules organiques au moyen des techniques de spectrométrie de masse,
This course provides a basic foundation in organic
chemistry and polymer chemistry, including chemical nomenclature of organic compounds and polymers, an understanding of chemical structures, chemical
A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compounds do undergo nucleophilic substitution. Just as normally nucleophilic alkenes can be made to undergo conjugate substitution if they carry electron-withdrawing substituents, so normally nucleophilic aromatic rings also become electrophilic if they have the right substituents.
In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate.R. A. Rossi, R. H. de Rossi, Aromatic Substitution by the SRN1 Mechanism, ACS Monograph Series No. 178, American Chemical Society, 1983. .
Water () is a polar inorganic compound that is at room temperature a tasteless and odorless liquid, which is nearly colorless apart from an inherent hint of blue. It is by far the most studied chemical compound and is described as the "universal solvent" and the "solvent of life". It is the most abundant substance on the surface of Earth and the only common substance to exist as a solid, liquid, and gas on Earth's surface. It is also the third most abundant molecule in the universe (behind molecular hydrogen and carbon monoxide).
Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) ...
WILEY-V C H VERLAG GMBH2022
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The Wacker process, which is widely used to convert monosubstituted alkenes into the corresponding methyl ketones, is thought to proceed through a PdII/Pd0 catalytic cycle involving a b-hydride elimination step. This mechanistic scenario is inapplicable to ...
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