[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
  The 3d structure may be viewed using Java or Javascript.
• 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
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
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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

Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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

Gas phase ion energetics 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₁₆H₁₆⁺ (ion structure unspecified)

Ionization energy determinations

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.

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]

Andrews and Westrum, 1970
Andrews, J.T.S.; Westrum, E.F., Jr., The heat capacity and thermodynamic functions of crystalline and liquid triptycene, J. Chem. Thermodynam., 1970, 2, 245-253. [all data]

Shieh, McNally, et al., 1969
Shieh, C.; McNally, D.; Boyd, R.H., The heats of combustion and strain energies of some cyclophanes, Tetrahedron, 1969, 3653-3665. [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, 2
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]

Gleiter, Eckert-Maksic, et al., 1982
Gleiter, R.; Eckert-Maksic, M.; Schafer, W.; Truesdale, E.A., Quest for a strong through bond interaction in [2.2]paracyclophane, Chem. Ber., 1982, 115, 2009. [all data]

Kovac, Mohraz, et al., 1980
Kovac, B.; Mohraz, M.; Heilbronner, E.; Boekelheide, V.; Hopf, H., Photoelectron spectra of the cyclophanes, J. Am. Chem. Soc., 1980, 102, 4314. [all data]

Heilbronner and Maier, 1974
Heilbronner, E.; Maier, J.P., Consequences of substitution in the photoelectron spectra of [2,2] paracyclophanes: separation of 'through-space' and 'through-bond' interactions as a consequence of fluorosubstitution, Helv. Chim. Acta, 1974, 57, 151. [all data]

Pignataro, Mancini, et al., 1971
Pignataro, S.; Mancini, V.; Ridyard, J.N.A.; Lempka, H.J., Photoelectron energy spectra of molecules having classically non-conjugated π-systems, Chem. Commun., 1971, 142. [all data]

Zhong-zhi, Kovak, et al., 1981
Zhong-zhi, Y.; Kovak, B.; Heilbronner, E.; Eltamany, S.; Hopf, H., 192. Ionization energies of methyl-substituted [2.2] paracyclophanes, Helv. Chim. Acta, 1981, 64, 1991. [all data]

Kovac, Allan, et al., 1980
Kovac, B.; Allan, M.; Heilbronner, E.; Maier, J.P.; Gleiter, R.; Haenel, M.W.; Keehn, P.M.; Reiss, J.A., He(Iα) photoelectron spectra of [2.2]cyclophanes, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 167. [all data]

Koenig, Wielesek, et al., 1975
Koenig, T.; Wielesek, R.; Snell, W.; Balle, T., Helium(I) photoelectron spectrum of p-quinodimethane, J. Am. Chem. Soc., 1975, 97, 3225. [all data]

Boschi and Schmidt, 1973
Boschi, R.; Schmidt, W., Transannular π - π interaction in cyclophanes, Angew. Chem. Int. Ed. Engl., 1973, 12, 402. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid 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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