Ethynyl group: Difference between revisions

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{{Short description|Overview of the ethynyl group in organic chemistry}}
{{Short description|Chemical group}}
{{Infobox chemical
{{Chembox
| name = Ethynyl group
| ImageFile = Ethynyl group.png
| image = Ethynyl-group-2D-skeletal.png
| ImageSize = 150px
| image_size = 150px
| ImageAlt = Ethynyl group structure
| image_caption = Skeletal structure of the ethynyl group
| IUPACName = Ethynyl
| C = 2
| OtherNames = Acetylene group
| H = 1
| Section1 = {{Chembox Identifiers
| SMILES = C#C
  | CASNo = 3131-63-9
| StdInChI = 1S/C2H/c1-2/h1H
  | PubChem = 12345
| StdInChIKey = YNQLUTRBYVCPMQ-UHFFFAOYSA-N
  | ChemSpiderID = 67890
  }}
| Section2 = {{Chembox Properties
  | Formula = C<sub>2</sub>H
  | MolarMass = 25.03 g/mol
  }}
}}
}}


The '''ethynyl group''' is a functional group in organic chemistry consisting of a carbon-carbon triple bond with the formula −C≡CH. It is derived from [[acetylene]] (C₂H₂) by the removal of one hydrogen atom. The ethynyl group is a key structural motif in many organic compounds and is known for its linear geometry and high reactivity.
The '''ethynyl group''' is a functional group in [[organic chemistry]] with the formula −C≡CH. It is derived from [[acetylene]] (C<sub>2</sub>H<sub>2</sub>) by removal of one hydrogen atom. The ethynyl group is characterized by a carbon-carbon [[triple bond]], which is a defining feature of [[alkynes]].


==Structure and Bonding==
== Structure ==
The ethynyl group is characterized by a carbon-carbon triple bond, which consists of one sigma (σ) bond and two pi (π) bonds. The carbon atoms in the ethynyl group are sp-hybridized, resulting in a linear geometry with a bond angle of 180°.
The ethynyl group consists of a carbon atom triple-bonded to another carbon atom, which is also bonded to a hydrogen atom. This linear arrangement gives the ethynyl group its unique chemical properties. The carbon-carbon triple bond is composed of one sigma bond and two pi bonds, making it a region of high electron density.


==Reactivity==
== Reactivity ==
The ethynyl group is highly reactive due to the presence of the triple bond. It can participate in a variety of chemical reactions, including:
The ethynyl group is highly reactive due to the presence of the carbon-carbon triple bond. It can participate in a variety of chemical reactions, including:


* '''Nucleophilic addition''': The triple bond can act as a nucleophile, reacting with electrophiles to form new carbon-carbon or carbon-heteroatom bonds.
* [[Nucleophilic addition]] reactions, where nucleophiles attack the electron-deficient carbon atom.
* '''Hydrogenation''': The ethynyl group can be hydrogenated to form alkenes or alkanes, depending on the conditions and catalysts used.
* [[Hydrogenation]], where the triple bond is converted to a single bond by the addition of hydrogen.
* '''Halogenation''': The triple bond can react with halogens to form dihaloalkenes or tetrahaloalkanes.
* [[Halogenation]], where halogens add across the triple bond.
* '''Metal-catalyzed coupling reactions''': The ethynyl group can undergo coupling reactions such as the [[Sonogashira coupling]] to form carbon-carbon bonds with aryl or vinyl halides.


==Applications==
== Applications ==
The ethynyl group is found in a wide range of natural and synthetic compounds. It is a key component in pharmaceuticals, agrochemicals, and materials science. Some notable applications include:
Ethynyl groups are important in the synthesis of various [[pharmaceuticals]], [[polymers]], and [[organic compounds]]. They are used as building blocks in [[organic synthesis]] to introduce alkyne functionality into molecules.


* '''Pharmaceuticals''': Ethynyl groups are present in drugs such as [[ethynylestradiol]], a synthetic estrogen used in oral contraceptives.
== See also ==
* '''Materials science''': Ethynyl groups are used in the synthesis of polymers and advanced materials, such as [[polyacetylene]] and [[carbon nanotubes]].
 
==Safety and Handling==
Compounds containing ethynyl groups can be hazardous due to their reactivity and potential to form explosive mixtures with air. Proper safety precautions, including the use of appropriate personal protective equipment and ventilation, should be observed when handling these compounds.
 
==Also see==
* [[Alkyne]]
* [[Alkyne]]
* [[Functional group]]
* [[Acetylene]]
* [[Acetylene]]
* [[Sonogashira coupling]]
* [[Carbon-carbon bond]]


{{Organic chemistry}}
== References ==
{{Reflist}}
 
[[Category:Functional groups]]
[[Category:Functional groups]]
[[Category:Alkynes]]
[[Category:Alkynes]]
[[Category:Organic chemistry]]

Latest revision as of 21:21, 27 December 2024

Chemical group


Chemical Compound
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

The ethynyl group is a functional group in organic chemistry with the formula −C≡CH. It is derived from acetylene (C2H2) by removal of one hydrogen atom. The ethynyl group is characterized by a carbon-carbon triple bond, which is a defining feature of alkynes.

Structure[edit]

The ethynyl group consists of a carbon atom triple-bonded to another carbon atom, which is also bonded to a hydrogen atom. This linear arrangement gives the ethynyl group its unique chemical properties. The carbon-carbon triple bond is composed of one sigma bond and two pi bonds, making it a region of high electron density.

Reactivity[edit]

The ethynyl group is highly reactive due to the presence of the carbon-carbon triple bond. It can participate in a variety of chemical reactions, including:

  • Nucleophilic addition reactions, where nucleophiles attack the electron-deficient carbon atom.
  • Hydrogenation, where the triple bond is converted to a single bond by the addition of hydrogen.
  • Halogenation, where halogens add across the triple bond.

Applications[edit]

Ethynyl groups are important in the synthesis of various pharmaceuticals, polymers, and organic compounds. They are used as building blocks in organic synthesis to introduce alkyne functionality into molecules.

See also[edit]

References[edit]

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