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Cyclopropyne

From Wikipedia, the free encyclopedia
Cyclopropyne
Names
Preferred IUPAC name
Cyclopropyne
Identifiers
3D model (JSmol)
  • InChI=1S/C3H2/c1-2-3-1/h1H2 checkY
    Key: WWVWWECUZUPLCL-UHFFFAOYSA-N checkY
  • C1C#C1
Properties
C3H2
Molar mass 38.049 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclopropyne is an extremely strained, unstable, and reactive cycloalkyne with the chemical formula C3H2.[1][2] As the smallest cycloalkyne, it features a three-carbon ring that includes a triple bond. The significant ring strain makes the compound challenging to produce and causes its high reactivity.[3]

Theoretical studies

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Although cyclopropyne is inherently unstable, it has been extensively investigated through theoretical studies aimed at exploring its electronic structure, energy properties, and vibrational characteristics. A similar compound called silacyclopropyne, in which a silicon atom substitutes one of the carbon atoms in the ring, has been successfully synthesized and examined.[4]

See also

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References

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  1. Dodziuk, Helena (30 March 2009). Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis. John Wiley & Sons. p. 376. ISBN 978-3-527-62714-1. Retrieved 7 August 2025.
  2. "Cyclopropyne properties - SpringerMaterials". Springer. Retrieved 7 August 2025.
  3. Saxe, Paul; Schaefer, Henry F. III (1 April 1980). "Can cyclopropyne really be made?". Journal of the American Chemical Society. 102 (9): 3239–3240. Bibcode:1980JAChS.102.3239S. doi:10.1021/ja00529a057. ISSN 0002-7863. Retrieved 7 August 2025.
  4. Brandow, Christopher G.; Allen, Wesley D.; Henry F., Schaefer III (31 July 1996). "Cyclopropyne and Silacyclopropyne: A World of Difference". ACS Publications. 118 (30): 7158–7163. Bibcode:1996JAChS.118.7158S. doi:10.1021/ja960762n. Retrieved 19 May 2026.