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
Δfgas37.5 ± 0.4kcal/molCmWiberg and Fenoglio, 1968ALS
Quantity Value Units Method Reference Comment
Δcgas-618.60 ± 0.36kcal/molCmWiberg and Fenoglio, 1968Corresponding Δfgas = 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

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
5.90260.AStephenson and Malanowski, 1987Based on data from 206. to 275. K.; AC
5.88260.N/AHeisig, 1941Based on data from 196. to 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 to 275.14.076881009.32-28.164Heisig, 1941Coefficents calculated by NIST from author's data.

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:
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
Δr404.6 ± 1.5kcal/molCIDCTian, Fattahi, et al., 2006gas phase; B
Δr397.1 ± 5.1kcal/molG+TSKass, Filley, et al., 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr396.5 ± 1.6kcal/molH-TSTian, Fattahi, et al., 2006gas phase; B
Δr389.0 ± 5.0kcal/molIMRBKass, Filley, et al., 1986gas phase; B

References

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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]

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]

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]


Notes

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