chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a natural science that covers the elements that make up matter to the compounds made of atoms, molecules and ions: their composition, structure, proper ...

, electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic 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 processe ...

, electron-rich species have low

ionization energy Ionization, or Ionisation is the process by which an atom or a molecule acquires a negative or positive charge by gaining or losing electrons, often in conjunction with other chemical changes. The resulting electrically charged atom or molecule ...

and/or are

reducing agent In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are commonly reducing agents include the Earth met ...

s. Tetrakis(dimethylamino)ethylene is an electron-rich alkene because, unlike

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene ...

, it forms isolable

radical cation In organic chemistry, a radical anion is a free radical species that carries a negative charge. Radical anions are encountered in organic chemistry as reduced derivatives of polycyclic aromatic compounds, e.g. sodium naphthenide. An example of a ...

. In contrast, electron-poor alkene

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 malononitri ...

is an electron acceptor, forming isolable anions. *with regards to acid-base reactions, electron-rich species have high

pKa PKA may refer to: * Professionally known as: ** Pen name ** Stage persona * p''K''a, the symbol for the acid dissociation constant at logarithmic scale * Protein kinase A, a class of cAMP-dependent enzymes * Pi Kappa Alpha, the North-American so ...

's and react with weak

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 ...

s. *with regards to nucleophilic substitution reactions, electron-rich species are relatively strong nucleophiles, as judged by rates of attack by electrophiles. For example, compared to

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

pyrrole Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-meth ...

is more rapidly attacked by electrophiles. Pyrrole is therefore considered to be an electron-rich aromatic ring. Similarly, benzene derivatives with electron-donating groups (EDGs) are attacked by electrophiles faster than in benzene. The electron-donating vs electron-withdrawing influence of various functional groups have been extensively parameterized in

linear free energy relationship In physical organic chemistry, a free-energy relationship or Gibbs energy relation relates the logarithm of a reaction rate constant or equilibrium constant for one series of chemical reactions with the logarithm of the rate or equilibrium const ...

s. *with regards to

ity, electron-rich species are strong

Lewis base 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 ...

s.{{cite journal , doi=10.1021/ar9501479, title=Recognition of Electron-Donating Guests by Carborane-Supported Multidentate Macrocyclic Lewis Acid Hosts: Mercuracarborand Chemistry , year=1997 , last1=Hawthorne , first1=M. Frederick , last2=Zheng , first2=Zhiping , journal=Accounts of Chemical Research , volume=30 , issue=7 , pages=267–276

References

Physical_organic_chemistry.html" ;"title="trinitrobenzene.html" ;"title="benzene, trinitrobenzene">benzene, trinitrobenzene forms adducts --> Physical organic chemistry">trinitrobenzene.html" ;"title="benzene, trinitrobenzene">benzene, trinitrobenzene forms adducts --> Physical organic chemistry Chemical bonding