Cyclopropyne

Last updated
Cyclopropyne
Cyclopropyne.svg
Cyclopropyne 2.svg
Names
Preferred IUPAC name
Cyclopropyne
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C3H2/c1-2-3-1/h1H2 Yes check.svgY
    Key: WWVWWECUZUPLCL-UHFFFAOYSA-N Yes check.svgY
  • 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]

Contents

Theoretical studies

Although cyclopropyne is challenging to isolate, 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] [5]

See also

References

  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 7 August 2025.
  5. ↑ Sherrill, C. David; Brandow, Christopher G.; Allen, Wesley D.; Schaefer, Henry F. (1 January 1996). "Cyclopropyne and Silacyclopropyne: A World of Difference" . Journal of the American Chemical Society . 118 (30): 7158–7163. Bibcode:1996JAChS.118.7158S. doi:10.1021/ja960762n. ISSN   0002-7863 . Retrieved 7 August 2025.
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