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Cyclobutane

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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: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
34.1550.Dorofeeva O.V., 1986Discrepancies between selected values and those calculated earlier [ Rathjens G.W., 1953] increase as the temperature increases and amount to 5.4 and 3.1 J/mol*K for S(1500 K) and Cp(1500 K), respectively.
38.19100.
42.28150.
48.84200.
64.23273.15
70.6 ± 1.5298.15
71.05300.
97.67400.
122.03500.
142.64600.
159.92700.
174.52800.
186.99900.
197.671000.
206.851100.
214.761200.
221.591300.
227.501400.
232.621500.

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
Deltacliquid-2720.4 ± 0.5kJ/molCcbKaarsemaker and Coops, 1952Corresponding «DELTA»fliquid = 3.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-2720.5 ± 0.4kJ/molCcbCoops and Kaarsemaker, 1950Corresponding «DELTA»fliquid = 3.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid175.15J/mol*KN/ARathjens and Gwinn, 1953DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
106.32285.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, Kenneth Kroenlein 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
Deltavap23.92kJ/molN/AMajer and Svoboda, 1985 
Deltavap23.2kJ/molVKaarsemaker and Coops, 1952ALS
Deltavap23.3 ± 0.4kJ/molVCoops and Kaarsemaker, 1950ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
24.188285.66N/ARathjens and Gwinn, 1953P = 101.325 kPa; DH
24.19285.7N/AMajer and Svoboda, 1985 
25.2272.AStephenson and Malanowski, 1987Based on data from 198. - 287. K.; AC
5.781559.CRathjens and Gwinn, 1953, 2ALS
25.2270.N/ARathjens and Gwinn, 1953Based on data from 217. - 285. K. See also Boublik, Fried, et al., 1984.; AC

Entropy of vaporization

DeltavapS (J/mol*K) Temperature (K) Reference Comment
84.67285.66Rathjens and Gwinn, 1953P; DH

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
213.22 - 285.344.071431038.009-30.334Rathjens and Gwinn, 1953Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
36.4145.BBondi, 1963AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
1.09182.4Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
39.17145.7Domalski and Hearing, 1996CAL
5.96182.4

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
5.707145.7crystaline, IIcrystaline, IRathjens and Gwinn, 1953Transition over about 120 to 145.7 K. Values represent excess over extrapolated Cp curves.; DH
1.088182.42crystaline, IliquidRathjens and Gwinn, 1953DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
39.17145.7crystaline, IIcrystaline, IRathjens and Gwinn, 1953Transition; DH
5.96182.42crystaline, 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:


Reaction 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C4H7- + Hydrogen cation = Cyclobutane

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Deltar1746. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase; B
Deltar1757. ± 8.4kJ/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Quantity Value Units Method Reference Comment
Deltar1709. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase; B
Deltar1719. ± 8.8kJ/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B

2Ethylene = Cyclobutane

By formula: 2C2H4 = C4H8

Quantity Value Units Method Reference Comment
Deltar-86.6 ± 4.2kJ/molEqkQuick, Knecht, et al., 1972gas phase; At 750 K; ALS

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
Deltar1746. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase; B
Deltar1757. ± 8.4kJ/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Quantity Value Units Method Reference Comment
Deltar1709. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase; B
Deltar1719. ± 8.8kJ/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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Additional Data

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Owner NIST Mass Spectrometry Data Center
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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Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   D2d     Symmetry Number sigma = 4


 Sym.   No   Approximate   Selected Freq.  Infrared   Raman   Comments 
 Species   type of mode   Value   Rating   Value  Phase  Value  Phase

a1 1 CH2 s-str 2895  D  ia 2916 p liq. FR(2«nu»2,2«nu»13)
a1 1 CH2 s-str 2895  D  ia 2866 p liq. FR(2«nu»2,2«nu»13)
a1 2 CH2 scis 1443  C  ia 1443 p liq. SF(«nu»13)
a1 3 Ring str 1001  C  ia 1001 p liq. SF(«nu»14)
a1 4 CH2 a-str 2975  E  ia CF
a1 5 CH2 rock 741  C  ia 741 dp liq.
a1 6 Ring puck 197  C  ia 197 liq. CF
a2 7 CH2 wag 1260  E  ia  ia CF
a2 8 CH2 twist 1257  E  ia  ia CF
b1 9 CH2 wag 1219  C  ia 1219 dp liq.
b1 10 Ring deform 926  C  ia 926 dp liq.
b1 11 CH2 twist 1222  E  ia CF
b2 12 CH2 s-str 2893  E CF
b2 13 CH2 scis 1443  C 1443 dp liq. SF(«nu»2)
b2 14 Ring deform 1001  D 1001 p liq. SF(«nu»3)
b2 15 CH2 a-str 2987  C 2987 S gas
b2 16 CH2 rock 627  C 627 S gas
e 17 CH2 a-str 2952  C 2952 liq.
e 18 CH2 twist 1223  C 1223 W gas
e 19 CH2 rock 749  C 749 W gas
e 20 CH2 s-str 2887  D 2897 S gas
e 20 CH2 s-str 2887  D 2878 S gas
e 21 CH2 scis 1447  C 1447 S gas
e 22 CH2 wag 1257  C 1257 S gas
e 23 Ring deform 898  C 898 S gas

Source: Shimanouchi, 1972

Notes

SStrong
WWeak
iaInactive
pPolarized
dpDepolarized
FRFermi resonance with an overtone or a combination tone indicated in the parentheses.
CFCalculated frequency
SFCalculation shows that the frequency approximately equals that of the vibration indicated in the parentheses.
C3~6 cm-1 uncertainty
D6~15 cm-1 uncertainty
E15~30 cm-1 uncertainty

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedSqualane27.462.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.464.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.465.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.467.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free Links, Notes

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

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Rathjens G.W., 1953
Rathjens G.W., Jr., Infrared absorption spectra, structure and thermodynamic properties of cyclobutane, J. Am. Chem. Soc., 1953, 75, 5634-5642. [all data]

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]

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]

Quick, Knecht, et al., 1972
Quick, L.M.; Knecht, D.A.; Back, M.H., Kinetics of the formation of cyclobutane from ethylene, Int. J. Chem. Kinet., 1972, 4, 61-68. [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]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free Links, References