[2.2]Paracyclophane

• Formula: C₁₆H₁₆
• Molecular weight: 208.2982
• IUPAC Standard InChI: InChI=1S/C16H16/c1-2-14-4-3-13(1)9-10-15-5-7-16(8-6-15)12-11-14/h1-8H,9-12H2 Copy

  
• IUPAC Standard InChIKey: OOLUVSIJOMLOCB-UHFFFAOYSA-N Copy
• CAS Registry Number: 1633-22-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene; Cyclobis(benzene-1,4-dimethylene); Di-p-xylylene; Di-1,4-xylylene; tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
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Gas phase thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

IR Spectrum

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

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

Nishiyama, Sakiyama, et al., 1980
Nishiyama, K.; Sakiyama, N.; Seki, S.; Horita, H.; Otsubo, T.; Misumi, S., Thermochemical studies on double- and triple-layered [2.2]paracyclophanes. Estimation of molecular strain energies., Bull. Chem. Soc. Jpn., 1980, 53, 869-877. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Rodgers, Westrum, et al., 1973
Rodgers, D.L.; Westrum, E.F., Jr.; Andrews, J.T.S., The enthalpies of combustion and formation of [2.2]-paracyclophane and triptycene, J. Chem. Thermodyn., 1973, 5, 733-739. [all data]

Boyd, 1966
Boyd, R.H., The heat of combustion and strain energy of 2,2-paracyclophane, Tetrahedron, 1966, 22, 119-122. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Andrews and Westrum, 1970
Andrews, John T.S.; Westrum, Edgar F., Heat capacity and thermodynamic properties of [2.2]paracyclophane. Mechanism of the 50.deg.K transition, J. Phys. Chem., 1970, 74, 10, 2170-2174, https://doi.org/10.1021/j100909a022 . [all data]

Cram, Dalton, et al., 1963
Cram, D.J.; Dalton, C.K.; Knox, G.R., Macro rings. XXIX. Stereochemistry of a 1,6-cycloaddition reaction, J. Am. Chem. Soc., 1963, 85, 1088-1093. [all data]

Notes

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• Symbols used in this document:
  

  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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