| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Cyclopropyne | |||
| Identifiers | |||
3D model (JSmol)
|
|||
PubChem CID
|
|||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
| 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 C3H2.12 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
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
References
References
- 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.
- "Cyclopropyne properties - SpringerMaterials". Springer. Retrieved 7 August 2025.
- 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.
- 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.