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-ene

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Suffix used in organic chemistry
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ene reaction coupled with orbital interactions and thetransition state

Thesuffix-ene is used inorganic chemistry to form names of organic compounds where the -C=C- group has been attributed the highest priority according to the rules oforganic nomenclature.[1][2] Sometimes a number betweenhyphens is inserted before it to say that thedouble bond is between that atom and the atom with the next number up. This suffix comes from the end of the wordethylene, which is the simplestalkene. The final "-e" disappears if it comes before by a suffix that starts with avowel, e.g. "-enal", which is a compound that contains both a -C=C- bond and analdehyde functional group. If the other suffix starts with aconsonant or "y", the final "-e" remains,e.g. "-enediyne" (which has the "-ene" suffix and also the "-yne" suffix, for a compound with adouble bond and twotriple bonds.)

Usage

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A Greek number prefix before the "-ene" indicates how many double bonds there are in the compound, e.g.butadiene.[3] The suffix is defined from anene reaction.[4]

The suffix "-ene" is also used ininorganic chemistry to indicate a one-atom thick two-dimensional layer of atoms, as ingraphene,silicene,stanene,borophene, xenzophene, andgermanene.

Etymology

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The suffix -ene was originally a Greek name-forming element without its own meaning. Its was used early on in the names ofethylene andmethylene, the later being an alcohol rather than an alkene. It was first abstracted a formal naming system for the alkenes byAugust Wilhelm von Hofmann in 1866, whose proposed a vowel system (-ane, -ene, ine, -one, -une) to denotehydrocarbons of increasing degrees of desaturation.[5][6]

Despite graphene not being an alkene,Hanns-Peter Boehm and his colleagues used the -ene suffix because of graphene'saromatic, cyclic hydrocarbon structure.[7] Similar allotropes such asstanene andborophene, which are made of other elements, contain the suffix -ene in a manner analogous to graphene.

See also

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References

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  1. ^The Commission on the Nomenclature of Organic Chemistry (1971) [1958].Nomenclature of Organic Chemistry (A: Hydrocarbons, and B: Fundamental Heterocyclic Systems), 1965 (C: Characteristic Groups) (3 ed.). London: Butterworths.ISBN 0-408-70144-7.
  2. ^"7.4: Naming Alkenes".Chemistry LibreTexts. 2015-05-03. Retrieved2025-07-17.
  3. ^"-ene - (Organic Chemistry) - Vocab, Definition, Explanations | Fiveable".library.fiveable.me.
  4. ^"Ene Reactions".Chemistry LibreTexts. November 11, 2013.
  5. ^Hofmann, A. W. (1866)."On the Action of Trichloride of Phosphorus on the Salts of the Aromatic Monamines".Proceedings of the Royal Society of London.15:54–62.ISSN 0370-1662.
  6. ^"Alkane Nomenclature".chem125-oyc.webspace.yale.edu. Retrieved2025-07-17.
  7. ^Boehm, H. P.; Setton, R.; Stumpp, E. (1986-01-01)."Nomenclature and terminology of graphite intercalation compounds".Carbon.24 (2):241–245.doi:10.1016/0008-6223(86)90126-0.ISSN 0008-6223.
Look up-ene in Wiktionary, the free dictionary.
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