[2.2]Paracyclophane

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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

Quantity Value Units Method Reference Comment
Δfgas244.7 ± 2.1kJ/molCcbNishiyama, Sakiyama, et al., 1980Reanalyzed by Cox and Pilcher, 1970, Original value = 246.3 ± 3.3 kJ/mol
Δfgas241. ± 4.2kJ/molCcbRodgers, Westrum, et al., 1973 
Δfgas241.3 ± 4.3kJ/molCcbBoyd, 1966Reanalyzed by Cox and Pilcher, 1970, Original value = 251. ± 7.9 kJ/mol

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

Quantity Value Units Method Reference Comment
Δfsolid146.7 ± 2.8kJ/molCcbNishiyama, Sakiyama, et al., 1980ALS
Δfsolid144.7 ± 0.88kJ/molCcbRodgers, Westrum, et al., 1973ALS
Δfsolid154. ± 4.kJ/molCcbBoyd, 1966ALS
Quantity Value Units Method Reference Comment
Δcsolid-8729.5 ± 1.8kJ/molCcbNishiyama, Sakiyama, et al., 1980Corresponding Δfsolid = 146.68 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-8727.57 ± 0.63kJ/molCcbRodgers, Westrum, et al., 1973Corresponding Δfsolid = 144.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-8737. ± 4.kJ/molCcbBoyd, 1966Corresponding Δfsolid = 154. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar265.68J/mol*KN/AAndrews and Westrum, 1970DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
252.7298.15Rodgers, Westrum, et al., 1973Cp given as 0.290 cal/g*K.; DH
252.34298.15Andrews and Westrum, 1970T = 10 to 350 K.; DH
248.1300.Shieh, McNally, et al., 1969T = 300, 318 K.; DH

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

Quantity Value Units Method Reference Comment
Δsub98.0kJ/molN/ANishiyama, Sakiyama, et al., 1980DRB
Δsub96.2 ± 4.2kJ/molVRodgers, Westrum, et al., 1973ALS
Δsub96.3kJ/molN/ARodgers, Westrum, et al., 1973DRB
Δsub96.2 ± 4.2kJ/molVBoyd, 1966ALS
Δsub87.3kJ/molN/ABoyd, 1966DRB

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
99.6 ± 1.8381.4VNishiyama, Sakiyama, et al., 1980ALS
96.4 ± 1.5353. to 409.TSGCNishiyama, Sakiyama, et al., 1980AC
92.9 ± 0.84363.MEBoyd, 1966Based on data from 343. to 383. K. See also Stephenson and Malanowski, 1987 and Cox and Pilcher, 1970, 2.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
0.21323.2Andrews and Westrum, 1970, 2AC

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

IE (eV) Method Reference Comment
7.8PEGleiter, Eckert-Maksic, et al., 1982LBLHLM
7.8PEKovac, Mohraz, et al., 1980LLK
7.60PEHeilbronner and Maier, 1974LLK
~7.8PIPignataro, Mancini, et al., 1971LLK
8.2PEGleiter, Eckert-Maksic, et al., 1982Vertical value; LBLHLM
8.10PEZhong-zhi, Kovak, et al., 1981Vertical value; LLK
8.10PEKovac, Allan, et al., 1980Vertical value; LLK
8.00PEKoenig, Wielesek, et al., 1975Vertical value; LLK
8.08PEBoschi and Schmidt, 1973Vertical value; LLK

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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