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Cyclobutene

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas37.5 ± 0.4kcal/molCmWiberg and Fenoglio, 1968ALS
Quantity Value Units Method Reference Comment
Deltacgas-618.60 ± 0.36kcal/molCmWiberg and Fenoglio, 1968Corresponding «DELTA»fgas = 37.45 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
7.96450.Dorofeeva O.V., 1986Discrepancies between selected values and those calculated earlier [ Danti A., 1957] amount to 1.6-3.5 J/mol*K for S(T) and Cp(T).; GT
8.377100.
9.228150.
10.68200.
14.04273.15
15.39 ± 0.48298.15
15.50300.
21.05400.
25.961500.
30.005600.
33.327700.
36.099800.
38.439900.
40.4351000.
42.1461100.
43.6161200.
44.8851300.
45.9821400.
46.9361500.

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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil275.2KN/AWeast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
5.90260.AStephenson and Malanowski, 1987Based on data from 206. - 275. K.; AC
5.88260.N/AHeisig, 1941Based on data from 196. - 275. K. See also Boublik, Fried, et al., 1984.; AC

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
196.0 - 275.14.076881009.32-28.164Heisig, 1941Coefficents calculated by NIST from author's data.

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 by: John E. Bartmess

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

cyclobutene-1-ide anion + Hydrogen cation = Cyclobutene

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Deltar404.6 ± 1.5kcal/molCIDCTian, Fattahi, et al., 2006gas phase
Deltar397.1 ± 5.1kcal/molG+TSKass, Filley, et al., 1986gas phase
Quantity Value Units Method Reference Comment
Deltar396.5 ± 1.6kcal/molH-TSTian, Fattahi, et al., 2006gas phase
Deltar389.0 ± 5.0kcal/molIMRBKass, Filley, et al., 1986gas phase

(CAS Reg. No. 60211-41-8 bullet 4294967295Cyclobutene) + Cyclobutene = CAS Reg. No. 60211-41-8

By formula: (CAS Reg. No. 60211-41-8 bullet 4294967295C4H6) + C4H6 = CAS Reg. No. 60211-41-8

Quantity Value Units Method Reference Comment
Deltar13.7 ± 2.1kcal/molN/ADePuy, Gronert, et al., 1989gas phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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
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 C4H6+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.43 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)187.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity180.1kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.43 ± 0.02PEBieri, Burger, et al., 1977LLK
9.43PEBischof and Heilbronner, 1970RDSH
9.59PEWiberg, Ellison, et al., 1976Vertical value; LLK
9.43 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
9.43PEClary, Lewis, et al., 1974Vertical value; LLK

De-protonation reactions

cyclobutene-1-ide anion + Hydrogen cation = Cyclobutene

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Deltar404.6 ± 1.5kcal/molCIDCTian, Fattahi, et al., 2006gas phase; B
Deltar397.1 ± 5.1kcal/molG+TSKass, Filley, et al., 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar396.5 ± 1.6kcal/molH-TSTian, Fattahi, et al., 2006gas phase; B
Deltar389.0 ± 5.0kcal/molIMRBKass, Filley, et al., 1986gas phase; B

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes

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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Due to licensing restrictions, this spectrum cannot be downloaded.

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.
Origin Chemical Concepts
NIST MS number 151947

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References

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

Wiberg and Fenoglio, 1968
Wiberg, K.B.; Fenoglio, R.A., Heats of formation of C4H6 hydrocarbons, J. Am. Chem. Soc., 1968, 90, 3395-3397. [all data]

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]

Danti A., 1957
Danti A., Thermodynamic functions of cyclobutene, J. Chem. Phys., 1957, 27, 1227. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Heisig, 1941
Heisig, G.B., The Preparation and the Vapor Pressures of Cyclobutene and Cyclobutane *, J. Am. Chem. Soc., 1941, 63, 6, 1698-1699, https://doi.org/10.1021/ja01851a055 . [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]

Tian, Fattahi, et al., 2006
Tian, Z.X.; Fattahi, A.; Lis, L.; Kass, S.R., Cycloalkane and cycloalkene C-H bond dissociation energies, J. Am. Chem. Soc., 2006, 128, 51, 17087-17092, https://doi.org/10.1021/ja065348u . [all data]

Kass, Filley, et al., 1986
Kass, S.R.; Filley, J.; Van Doren, J.M.; DePuy, C.H., Nitrous oxide in gas-phase ion-molecule chemistry: A versatile reagent for the determination of carbanion structure, J. Am. Chem. Soc., 1986, 108, 2849. [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]

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]

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]

Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E., Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen, Helv. Chim. Acta, 1970, 53, 1677. [all data]

Wiberg, Ellison, et al., 1976
Wiberg, K.B.; Ellison, G.B.; Wendoloski, J.J.; Brundle, C.R.; Kuebler, N.A., Electronic states of organic molecules. 3. Photoelectron spectra of cycloalkenes and methylenecycloalkanes, J. Am. Chem. Soc., 1976, 98, 7179. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A<--2X and 2B<--2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Clary, Lewis, et al., 1974
Clary, D.C.; Lewis, A.A.; Morland, D.; Murrell, J.N.; Heilbronner, E., Ionization potentials of cycloalkenes, J. Chem. Soc. Faraday Trans. 2, 1974, 70, 1889. [all data]


Notes

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