Adduct
Encyclopedia
An adduct is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is considered a distinct molecular species. Examples include the adduct between hydrogen peroxide
and sodium carbonate
to give sodium percarbonate
, and the addition of sodium bisulfite
to an aldehyde
to give a sulfonate
.
Adducts often form between Lewis acid
s and Lewis bases. A good example is the formation of adducts between the Lewis acid borane
and the oxygen atom in the Lewis bases, tetrahydrofuran
(THF): BH3•O(CH2)4 or diethyl ether
: BH3•O(CH3CH2)2.
Compounds or mixtures that cannot form an adduct because of steric hindrance are called frustrated Lewis pair
s.
Adducts are not necessarily molecular in nature. A good example from solid-state chemistry
is the adducts of ethylene or carbon monoxide of CuAlCl4. The latter is a solid with an extended lattice structure. Upon formation of the adduct, a new extended phase is formed in which the gas molecules are incorporated (inserted) as ligand
s of the copper atoms within the structure. This reaction can also be considered a reaction between a base and a Lewis acid with the copper atom in the electron-receiving and the pi electrons of the gas molecule in the donating role.
Hydrogen peroxide
Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...
and sodium carbonate
Sodium carbonate
Sodium carbonate , Na2CO3 is a sodium salt of carbonic acid. It most commonly occurs as a crystalline heptahydrate, which readily effloresces to form a white powder, the monohydrate. Sodium carbonate is domestically well-known for its everyday use as a water softener. It can be extracted from the...
to give sodium percarbonate
Sodium percarbonate
Sodium percarbonate is a chemical, an adduct of sodium carbonate and hydrogen peroxide , with formula Na2CO3 · 1.5H2O2. It is a colorless, crystalline, hygroscopic and water-soluble solid...
, and the addition of sodium bisulfite
Sodium bisulfite
Sodium bisulfite is a chemical compound with the chemical formula NaHSO3. Sodium bisulfite is a food additive with E number E222. This salt of bisulfite can be prepared by bubbling sulfur dioxide in a solution of sodium carbonate in water...
to an aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
to give a sulfonate
Sulfonate
A sulfonate is a salt or ester of a sulfonic acid. It contains the functional group R-SO2O-.- Sulfonate salts:Anions with the general formula RSO2O− are called sulfonates. They are the conjugate bases of sulfonic acids with formula RSO2OH. As sulfonic acids tend to be strong acids, the...
.
Adducts often form between Lewis acid
Lewis acid
]The term Lewis acid refers to a definition of acid published by Gilbert N. Lewis in 1923, specifically: An acid substance is one which can employ a lone pair from another molecule in completing the stable group of one of its own atoms. Thus, H+ is a Lewis acid, since it can accept a lone pair,...
s and Lewis bases. A good example is the formation of adducts between the Lewis acid borane
Borane
In chemistry, a borane is a chemical compound of boron and hydrogen. The boranes comprise a large group of compounds with the generic formulae of BxHy. These compounds do not occur in nature. Many of the boranes readily oxidise on contact with air, some violently. The parent member BH3 is called...
and the oxygen atom in the Lewis bases, tetrahydrofuran
Tetrahydrofuran
Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...
(THF): BH3•O(CH2)4 or diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
: BH3•O(CH3CH2)2.
Compounds or mixtures that cannot form an adduct because of steric hindrance are called frustrated Lewis pair
Frustrated Lewis pair
In chemistry, a frustrated Lewis pair is a compound or mixture containing a Lewis acid and a Lewis base that, because of steric hindrance, cannot combine to form an adduct...
s.
Adducts are not necessarily molecular in nature. A good example from solid-state chemistry
Solid-state chemistry
Solid-state chemistry, also sometimes referred to as materials chemistry, is the study of the synthesis, structure, and properties of solid phase materials, particularly, but not necessarily exclusively of, non-molecular solids...
is the adducts of ethylene or carbon monoxide of CuAlCl4. The latter is a solid with an extended lattice structure. Upon formation of the adduct, a new extended phase is formed in which the gas molecules are incorporated (inserted) as ligand
Ligand
In coordination chemistry, a ligand is an ion or molecule that binds to a central metal atom to form a coordination complex. The bonding between metal and ligand generally involves formal donation of one or more of the ligand's electron pairs. The nature of metal-ligand bonding can range from...
s of the copper atoms within the structure. This reaction can also be considered a reaction between a base and a Lewis acid with the copper atom in the electron-receiving and the pi electrons of the gas molecule in the donating role.