Cubane

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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 as indicated in comments:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δvap10.7 ± 0.2kcal/molCGCBashir-Hashemi, Chickos, et al., 2004AC
Quantity Value Units Method Reference Comment
Δsub13.2 ± 0.48kcal/molAC+CGCBashir-Hashemi, Chickos, et al., 2004AC
Δsub  MEKybett, Carroll, et al., 1966uncertain value: 19.2 ± 0.38 kcal/mol; in Ref. Diky, Frenkel, et al., 2003 the authors state that the value of 80.3 kJ/mole from Kybett, Carroll, et al., 1966 pertains to the average temperature and not to 298 K. The authors give a value of 79.1±1.7 for the 298 K value; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
19.2 ± 0.4239.VKybett, Carroll, et al., 1966, 2ALS

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
2.1404.9ACWhite, Wasylishen, et al., 1992AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
3.604394.White, Wasylishen, et al., 1992, 2CAL
5.136404.9

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.420395.04crystaline, IIcrystaline, IWhite, Wasylishen, et al., 1992DH
2.079404.9crystaline, IliquidWhite, Wasylishen, et al., 1992DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
3.674395.04crystaline, IIcrystaline, IWhite, Wasylishen, et al., 1992DH
5.43404.9crystaline, IliquidWhite, Wasylishen, et al., 1992DH

Gas phase ion energetics data

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

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C8H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.6 ± 0.1eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)205.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity199.2kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.6 ± 0.1TRPILifshitz and Eaton, 1983LBLHLM
8.46PEGassman and Yamaguchi, 1979LLK
8.6PEBischof, Eaton, et al., 1978LLK
8.4 ± 0.1EIGross, 1972LLK
8.64 ± 0.10EIFranklin and Carroll, 1969RDSH
8.74PEDewar and Worley, 1969RDSH
8.74 ± 0.15EIKybett, Carroll, et al., 1966, 2RDSH
9.00PEBischof, Eaton, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+10.01 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+14.33 ± 0.202C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H3+14.96 ± 0.102C2H2+HEIFranklin and Carroll, 1969RDSH
C4H4+12.88 ± 0.152C2H2EIFranklin and Carroll, 1969RDSH
C5H3+13.60 ± 0.10?EIFranklin and Carroll, 1969RDSH
C6H5+10.93 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C6H6+8.8 ± 0.1C2H2TRPILifshitz and Eaton, 1983LBLHLM
C6H6+9.2 ± 0.1?EIGross, 1972LLK
C6H6+9.00 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C8H6+8.92 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C8H7+9.3 ± 0.2HTRPILifshitz and Eaton, 1983LBLHLM
C8H7+8.96 ± 0.10HEIFranklin and Carroll, 1969RDSH

De-protonation reactions

C8H7- + Hydrogen cation = Cubane

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Δr403.4 ± 3.1kcal/molG+TSHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B
Quantity Value Units Method Reference Comment
Δr396.5 ± 3.0kcal/molIMRBHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B

References

Go To: Top, 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.

Bashir-Hashemi, Chickos, et al., 2004
Bashir-Hashemi, A.; Chickos, James S.; Hanshaw, William; Zhao, Hui; Farivar, Behzad S.; Liebman, Joel F., The enthalpy of sublimation of cubane, Thermochimica Acta, 2004, 424, 1-2, 91-97, https://doi.org/10.1016/j.tca.2004.05.022 . [all data]

Kybett, Carroll, et al., 1966
Kybett, B.D.; Carroll, S.; Natalis, P.; Bonnell, D.W.; Margrave, J.L.; Franklin, J.L., Thermodynamic Properties of Cubane, J. Am. Chem. Soc., 1966, 88, 3, 626-626, https://doi.org/10.1021/ja00955a056 . [all data]

Diky, Frenkel, et al., 2003
Diky, Vladimir V.; Frenkel, Michael; Karpushenkava, Larisa S., Thermodynamics of sublimation of cubane: natural anomaly or experimental error?, Thermochimica Acta, 2003, 408, 1-2, 115-121, https://doi.org/10.1016/S0040-6031(03)00318-6 . [all data]

Kybett, Carroll, et al., 1966, 2
Kybett, B.D.; Carroll, S.; Natalis, P.; Bonnell, D.W.; Margrave, J.L.; Franklin, J.L., Thermodynamic properties of cubane, J. Am. Chem. Soc., 1966, 88, 626. [all data]

White, Wasylishen, et al., 1992
White, M.A.; Wasylishen, R.E.; Eaton, P.E.; Xiong, Y.; Pramod, K.; Nodari, N., Orientational disorder in solid cubane: a thermodynamic and 13C NMR study, J. Phys. Chem., 1992, 96(1), 421-425. [all data]

White, Wasylishen, et al., 1992, 2
White, M.A.; Wasylishen, R.E.; Eaton, P.E.; Xiong, Y.; Pramod, K.; Nodari, N., Orientational disorder in solid cubane: a thermodynamic and carbon-13 NMR study, J. Phys. Chem., 1992, 96, 1, 421, https://doi.org/10.1021/j100180a078 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Lifshitz and Eaton, 1983
Lifshitz, C.; Eaton, P.E., Time-dependent mass spectra and breakdown graphs. III. The cubane cation complete or partial instability, Int. J. Mass Spectrom. Ion Phys., 1983, 49, 337. [all data]

Gassman and Yamaguchi, 1979
Gassman, P.G.; Yamaguchi, R., Electrochemical oxidation of strained hydrocarbons, J. Am. Chem. Soc., 1979, 101, 1308. [all data]

Bischof, Eaton, et al., 1978
Bischof, P.; Eaton, P.E.; Gleiter, R.; Heilbronner, E.; Jones, T.B.; Musso, H.; Schmelzer, A.; Stober, R., 44. The electronic structure of cubane (C8H8) as revealed by photoelectron spectroscopy, Helv. Chim. Acta, 1978, 61, 547. [all data]

Gross, 1972
Gross, M.L., Ion cyclotron resonance spectrometry. A means of evaluating 'kinetic shifts', Org. Mass Spectrom., 1972, 6, 827. [all data]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., The effect of molecular structure on ionic decomposition. I. An electron impact study of seven C8H8 isomers, J. Am. Chem. Soc., 1969, 91, 5940. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Hare, Emrick, et al., 1997
Hare, M.; Emrick, T.; Eaton, P.E.; Kass, S.R., Cubyl Anion Formation and an Experimental Determination of the Acidity and C-H Bond Dissociation Energy of Cubane, J. Am. Chem. Soc., 1997, 119, 1, 237, https://doi.org/10.1021/ja9627858 . [all data]


Notes

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