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Methylene group

From Wikipedia, the free encyclopedia
This article is about the functional group. For the compound, seeMethylene (compound).
Chemical group (–CH2–)
The hexamethylene diamine molecule contains six methylene groups

Amethylene group is any part of a molecule that consists of twohydrogen atomsbound to acarbon atom, which is connected to the remainder of the molecule by twosingle bonds.[1] The group may be represented as−CH2 or>CH2, where the '>' denotes the two bonds.

This stands in contrast to a situation where the carbon atom is bound to the rest of the molecule by adouble bond, which is preferably called amethylidene group, represented=CH2.[2] Formerly the methylene name was used for both isomers. The name "methylene bridge" can be used for the single-bonded isomer, to emphatically exclude methylidene. The distinction is often important, because the double bond is chemically different from two single bonds.

The methylene group should be distinguished from theCH2 molecule calledcarbene.[3] This was also formerly calledmethylene.

Activated methylene

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Acidity ofdiethyl malonate, a 1,3-dicarbonyl compound

The central carbon in1,3-dicarbonyl compound is known as anactivated methylene group. This is because, owing to the structure, the carbon is especially acidic and can easily be deprotonated to form a methylene group.[4]

See also

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References

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  1. ^"methylene (preferred IUPAC name"(PDF).
  2. ^"methylidene (preferred IUPAC name"(PDF).
  3. ^IUPAC,Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "carbenes".doi:10.1351/goldbook.C00806
  4. ^"Active Methylenes".
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