Methylidene group

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The blue part of this diagram of a propene molecule is a methylidene group. Propene Methylidene Structural Formulae V.1.svg
The blue part of this diagram of a propene molecule is a methylidene group.

In organic chemistry, a methylidene group is any part of a molecule that consists of two hydrogen atoms bound to a carbon atom, which is connected to the remainder of the molecule by a double bond. [1] The group may be represented as CH2=, where the '=' denotes the double bond.

This stands in contrast to methylene, the −CH2 group, which is connected to the rest of the molecule by two single bonds [2] The distinction is often important, because the double bond is chemically different from two single bonds.

3-Methylidenecycloprop-1-ene is named as a cyclopropene with a methylidene substituent. Methylenecyclopropene.svg
3-Methylidenecycloprop-1-ene is named as a cyclopropene with a methylidene substituent.

The same name (methylidene) was used for the distinct molecule CH2, also known as carbene. [3] Formerly the methylene name was used for all three isomers (methylene, methylidene, and carbene).

Many organic compounds are named and classified as if they were the result of substituting a methylidene group for two adjacent hydrogen atoms of some parent molecule (even if they are not actually obtained that way). Thus, for example, methylenecyclopropene is named after cyclopropene.

See also

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Methylene may refer to:

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n
H
2n - 2k + 2
, k > 0, where k is defined as the number of double bonds. There are no commercial sources.

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2
Ph
2
). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid.

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2
. It is a colourless gas that fluoresces in the mid-infrared range, and only persists in dilution, or as an adduct.

<span class="mw-page-title-main">Methylene group</span> Chemical group (–CH2–)

In organic chemistry, a methylene group is any part of a molecule that consists of two hydrogen atoms bound to a carbon atom, which is connected to the remainder of the molecule by two single bonds. The group may be represented as CH2<, where the '<' denotes the two bonds. This can equally well be represented as −CH2.

In organic chemistry, a methylene bridge, methylene spacer, or methanediyl group is any part of a molecule with formula −CH2; namely, a carbon atom bound to two hydrogen atoms and connected by single bonds to two other distinct atoms in the rest of the molecule. It is the repeating unit in the skeleton of the unbranched alkanes.

References

  1. "methylidene (preferred IUPAC name)" (PDF). p. 314.
  2. "methylene (preferred IUPAC name)" (PDF). p. 58.
  3. "methylidene (preferred IUPAC name)" (PDF). p. 921.