Cyclobutene
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChIKey: CFBGXYDUODCMNS-UHFFFAOYSA-N
- CAS Registry Number: 822-35-5
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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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 |
---|---|---|---|---|---|
ΔfH°gas | 157. ± 2. | kJ/mol | Cm | Wiberg and Fenoglio, 1968 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -2588.2 ± 1.5 | kJ/mol | Cm | Wiberg and Fenoglio, 1968 | Corresponding ΔfHºgas = 156.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.32 | 50. | Dorofeeva O.V., 1986 | Discrepancies 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 |
35.05 | 100. | ||
38.61 | 150. | ||
44.70 | 200. | ||
58.74 | 273.15 | ||
64.4 ± 2.0 | 298.15 | ||
64.84 | 300. | ||
88.07 | 400. | ||
108.62 | 500. | ||
125.54 | 600. | ||
139.44 | 700. | ||
151.04 | 800. | ||
160.83 | 900. | ||
169.18 | 1000. | ||
176.34 | 1100. | ||
182.49 | 1200. | ||
187.80 | 1300. | ||
192.39 | 1400. | ||
196.38 | 1500. |
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 |
---|---|---|---|---|---|
Tboil | 275.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.7 | 260. | A | Stephenson and Malanowski, 1987 | Based on data from 206. to 275. K.; AC |
24.6 | 260. | N/A | Heisig, 1941 | Based 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 (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
196.0 to 275.1 | 4.08259 | 1009.32 | -28.164 | Heisig, 1941 | Coefficents 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1693. ± 6.3 | kJ/mol | CIDC | Tian, Fattahi, et al., 2006 | gas phase |
ΔrH° | 1661. ± 21. | kJ/mol | G+TS | Kass, Filley, et al., 1986 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1659. ± 6.7 | kJ/mol | H-TS | Tian, Fattahi, et al., 2006 | gas phase |
ΔrG° | 1628. ± 21. | kJ/mol | IMRB | Kass, Filley, et al., 1986 | gas phase |
(CAS Reg. No. 60211-41-8 • 4294967295) +
= CAS Reg. No. 60211-41-8
By formula: (CAS Reg. No. 60211-41-8 • 4294967295C4H6) + C4H6 = CAS Reg. No. 60211-41-8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 57.3 ± 8.8 | kJ/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase |
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 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 784.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 753.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.43 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.43 | PE | Bischof and Heilbronner, 1970 | RDSH |
9.59 | PE | Wiberg, Ellison, et al., 1976 | Vertical value; LLK |
9.43 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
9.43 | PE | Clary, Lewis, et al., 1974 | Vertical value; LLK |
De-protonation reactions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1693. ± 6.3 | kJ/mol | CIDC | Tian, Fattahi, et al., 2006 | gas phase; B |
ΔrH° | 1661. ± 21. | kJ/mol | G+TS | Kass, Filley, et al., 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1659. ± 6.7 | kJ/mol | H-TS | Tian, Fattahi, et al., 2006 | gas phase; B |
ΔrG° | 1628. ± 21. | kJ/mol | IMRB | Kass, Filley, et al., 1986 | gas 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. |
---|---|
Origin | Chemical Concepts |
NIST MS number | 151947 |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Squalane | 27. | 432. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 433. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 433. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 434. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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]
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
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- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy Tboil Boiling point ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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