1,3-Bis(methylene)cyclobutane

• Formula: C₆H₈
• Molecular weight: 80.1277
• IUPAC Standard InChI: InChI=1S/C6H8/c1-5-3-6(2)4-5/h1-4H2 Copy

  
• IUPAC Standard InChIKey: DTSPMBOMCCTXSG-UHFFFAOYSA-N Copy
• CAS Registry Number: 2045-78-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Robert L. Brown and Stephen E. Stein

Reaction thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₆H₇^- +  =

By formula: C₆H₇^- + H⁺ = C₆H₈

2 +  =

By formula: 2H₂ + C₆H₈ = C₆H₁₂

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₆H₈⁺ (ion structure unspecified)

Ionization energy determinations

De-protonation reactions

C₆H₇^- +  =

By formula: C₆H₇^- + H⁺ = C₆H₈

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Hill and Squires, 1998
Hill, B.T.; Squires, R.R., Synthesis and Characterization of the Negative Ion of non-Kekule` Benzene, J. Chem. Soc. Perkin Trans., 1998, 2, 5, 1027, https://doi.org/10.1039/a707470k . [all data]

Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M., Heats of hydrogenation. VIII. Compounds with three- and four-membered rings, J. Am. Chem. Soc., 1968, 90, 4315-4322. [all data]

Hemmersbach, Klessinger, et al., 1978
Hemmersbach, P.; Klessinger, M.; Bruckmann, P., Electronic structure of exo-dimethylenecycloalkanes, J. Am. Chem. Soc., 1978, 100, 6344. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  Tboil	Boiling point
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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