chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...

, an electron-withdrawing group (EWG) is a

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...

that has some of the following kinetic and

thermodynamic Thermodynamics is a branch of physics that deals with heat, work, and temperature, and their relation to energy, entropy, and the physical properties of matter and radiation. The behavior of these quantities is governed by the four laws of ther ...

implications: *with regards to

electron transfer Electron transfer (ET) occurs when an electron relocates from an atom or molecule to another such chemical entity. ET is a mechanistic description of certain kinds of redox reactions involving transfer of electrons. Electrochemical processes ar ...

, electron-withdrawing groups enhance the oxidizing power tendency of the appended species.

Tetracyanoethylene Tetracyanoethylene (TCNE) is organic compound with the formula . It is a colorless solid, although samples are often off-white. It is an important member of the cyanocarbons. Synthesis and reactions TCNE is prepared by brominating malononitrile ...

is an oxidant because the alkene is appended to four cyano substituents, which are electron-withdrawing. *with regards to acid-base reactions, acids with electron-withdrawing groups species have low

acid dissociation constant In chemistry, an acid dissociation constant (also known as acidity constant, or acid-ionization constant; denoted ) is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction :HA ...

s. For EWG's attached to benzene, this effect is described by the

Hammett equation The Hammett equation in organic chemistry describes a linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para-substituents to each other with jus ...

, which allows EWGs to be discussed quantitatively. *with regards to

nucleophilic substitution reaction 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). Th ...

s, electron-withdrawing groups are susceptible to attack by weak

nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...

s. For example, compared to

chlorobenzene Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Uses Historical The major use of chlorob ...

chlorodinitrobenzene 2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the chemical formula (O2N)2C6H3Cl. It is a yellow solid that is soluble in organic solvents. It is an important intermediate for the industrial production of other compounds. DNCB is p ...

is susceptible to reactions that displace chloride.{{cite journal , author=J. F. Bunnett, R. M. Conner, doi=10.15227/orgsyn.040.0034, title=2,4-Dinitroiodobenzene , journal=Organic Syntheses , year=1960 , volume=40 , page=34 *electron-withdrawing substituents enhance the

Lewis acidity A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any s ...

. Relative to

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

, fluorine is a strong EWG. It follows that

boron trifluoride Boron trifluoride is the inorganic compound with the formula BF3. This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure and bondin ...

is a stronger

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...

than is

trimethylborane Trimethylborane (TMB) is a toxic, pyrophoric gas with the formula B(CH3)3 (which can also be written as Me3B, with Me representing methyl). Properties As a liquid it is colourless. The strongest line in the infrared spectrum is at 1330 cm� ...

References

Physical organic chemistry Chemical bonding