Cyclobutane

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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
Δcliquid-650.2 ± 0.1kcal/molCcbKaarsemaker and Coops, 1952Corresponding Δfliquid = 0.72 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-650.22 ± 0.1kcal/molCcbCoops and Kaarsemaker, 1950Corresponding Δfliquid = 0.74 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid41.862cal/mol*KN/ARathjens and Gwinn, 1953DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
25.411285.Rathjens and Gwinn, 1953T = 15 to 285 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
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

Quantity Value Units Method Reference Comment
Tboil284. ± 5.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus183.0KN/AKaarsemaker and Coops, 1952Uncertainty assigned by TRC = 1. K; TRC
Tfus193.KN/AWillstatter and Bruce, 1907Uncertainty assigned by TRC = 3. K; TRC
Tfus273.14KN/AWillstatter and Bruce, 1907Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Ttriple182.4 ± 0.6KAVGN/AAverage of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Δvap5.717kcal/molN/AMajer and Svoboda, 1985 
Δvap5.54kcal/molVKaarsemaker and Coops, 1952ALS
Δvap5.56 ± 0.1kcal/molVCoops and Kaarsemaker, 1950ALS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
5.7811285.66N/ARathjens and Gwinn, 1953P = 101.325 kPa; DH
5.782285.7N/AMajer and Svoboda, 1985 
6.02272.AStephenson and Malanowski, 1987Based on data from 198. to 287. K.; AC
1.382559.CRathjens and Gwinn, 1953, 2ALS
6.02270.N/ARathjens and Gwinn, 1953Based on data from 217. to 285. K. See also Boublik, Fried, et al., 1984.; AC

Entropy of vaporization

ΔvapS (cal/mol*K) Temperature (K) Reference Comment
20.24285.66Rathjens and Gwinn, 1953P; DH

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
213.22 to 285.344.065721038.009-30.334Rathjens and Gwinn, 1953Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
8.70145.BBondi, 1963AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
0.261182.4Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.362145.7Domalski and Hearing, 1996CAL
1.42182.4

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.364145.7crystaline, IIcrystaline, IRathjens and Gwinn, 1953Transition over about 120 to 145.7 K. Values represent excess over extrapolated Cp curves.; DH
0.2600182.42crystaline, IliquidRathjens and Gwinn, 1953DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
9.362145.7crystaline, IIcrystaline, IRathjens and Gwinn, 1953Transition; DH
1.42182.42crystaline, IliquidRathjens and Gwinn, 1953DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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 C4H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.8 ± 0.1eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.82 ± 0.05EIHolmes and Lossing, 1991LL
9.6 ± 0.1PEBieri, Burger, et al., 1977LLK
9.92 ± 0.05PERaymonda, 1972LLK
10.06EILossing, 1972LLK
≤10.3PIDoepker and Ausloos, 1966Personal communication from P. Natalis, B. Steiner, and M.G. Inghram; RDSH
10.7 ± 0.1PEBieri, Burger, et al., 1977Vertical value; LLK
10.7 ± 0.1PEBischof, Haselbach, et al., 1970Vertical value; RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H2+16.8?EIHughes and Tiernan, 1969RDSH
C2H3+17.7?EIHughes and Tiernan, 1969RDSH
C2H4+11.0 ± 0.15?EIMeisels, Park, et al., 1970RDSH
C2H5+13.8?EIHughes and Tiernan, 1969RDSH
C3H3+14.8?EIHughes and Tiernan, 1969RDSH
C3H5+11.00CH3EILossing, 1972LLK
C4H6+11.2 ± 0.1H2EIHolmes, Weese, et al., 1977LLK
C4H7+10.91HEILossing, 1972LLK

De-protonation reactions

C4H7- + Hydrogen cation = Cyclobutane

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Δr417.4 ± 2.0kcal/molBranDePuy, Gronert, et al., 1989gas phase; B
Δr419.9 ± 2.0kcal/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Quantity Value Units Method Reference Comment
Δr408.4 ± 2.1kcal/molH-TSDePuy, Gronert, et al., 1989gas phase; B
Δr410.9 ± 2.1kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B

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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Mass spectrum
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Additional Data

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Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 107

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

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

Kaarsemaker and Coops, 1952
Kaarsemaker, S.; Coops, J., Thermal quantities of some cycloparaffins. Part III. Results of measurements, Rec. Trav. Chim. Pays/Bas, 1952, 71, 261. [all data]

Coops and Kaarsemaker, 1950
Coops, J.; Kaarsemaker, SJ., Heat of combustion of cyclobutane, Recl. Trav. Chim. Pays-Bas, 1950, 69, 1364. [all data]

Rathjens and Gwinn, 1953
Rathjens, G.W., Jr.; Gwinn, W.D., Heat capacities and entropy of cyclobutane, J. Am. Chem. Soc., 1953, 75, 5629-5633. [all data]

Willstatter and Bruce, 1907
Willstatter, R.; Bruce, J., Chem. Ber., 1907, 40, 3979. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Rathjens and Gwinn, 1953, 2
Rathjens, G.W., Jr.; Gwinn, W.D., Heat capacities and entropy of cyclobutane, J. Am. Chem. Soc., 1953, 75, 5629-56. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Bondi, 1963
Bondi, A., Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments., J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Raymonda, 1972
Raymonda, J.W., Rydberg states in cyclic alkanes, J. Chem. Phys., 1972, 56, 3912. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions, Can. J. Chem., 1972, 50, 3973. [all data]

Doepker and Ausloos, 1966
Doepker, R.D.; Ausloos, P., Gas-phase radiolysis of cyclobutane, J. Chem. Phys., 1966, 44, 1641. [all data]

Bischof, Haselbach, et al., 1970
Bischof, P.; Haselbach, E.; Heilbronner, E., Photoelectron spectrum of cyclobutane, Angew. Chem. Int. Ed. Engl., 1970, 9, 953. [all data]

Hughes and Tiernan, 1969
Hughes, B.M.; Tiernan, T.O., Ionic reactions in gaseous cyclobutane, J. Chem. Phys., 1969, 51, 4373. [all data]

Meisels, Park, et al., 1970
Meisels, G.G.; Park, J.Y.; Giessner, B.G., Ionization and dissociation of C4H8 isomers, J. Am. Chem. Soc., 1970, 92, 254. [all data]

Holmes, Weese, et al., 1977
Holmes, J.L.; Weese, G.M.; Blair, A.S.; Terlouw, J.K., Metastable ion studies IX-Thermochemistry and ion structures among fragmenting [C4H8]+ ions, an electron impact and field ionization investigation, Org. Mass Spectrom., 1977, 12, 424. [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References