Cyclobutene
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChIKey: CFBGXYDUODCMNS-UHFFFAOYSA-N
- CAS Registry Number: 822-35-5
- Chemical structure:
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Gas phase thermochemistry data
Go To: Top, 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 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 | 37.5 ± 0.4 | kcal/mol | Cm | Wiberg and Fenoglio, 1968 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -618.60 ± 0.36 | kcal/mol | Cm | Wiberg and Fenoglio, 1968 | Corresponding ΔfHºgas = 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 |
---|---|---|---|
7.964 | 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 |
8.377 | 100. | ||
9.228 | 150. | ||
10.68 | 200. | ||
14.04 | 273.15 | ||
15.39 ± 0.48 | 298.15 | ||
15.50 | 300. | ||
21.05 | 400. | ||
25.961 | 500. | ||
30.005 | 600. | ||
33.327 | 700. | ||
36.099 | 800. | ||
38.439 | 900. | ||
40.435 | 1000. | ||
42.146 | 1100. | ||
43.616 | 1200. | ||
44.885 | 1300. | ||
45.982 | 1400. | ||
46.936 | 1500. |
Phase change data
Go To: Top, Gas phase thermochemistry 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 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 (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.90 | 260. | A | Stephenson and Malanowski, 1987 | Based on data from 206. to 275. K.; AC |
5.88 | 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 (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
196.0 to 275.1 | 4.07688 | 1009.32 | -28.164 | Heisig, 1941 | Coefficents calculated by NIST from author's data. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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 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° | 404.6 ± 1.5 | kcal/mol | CIDC | Tian, Fattahi, et al., 2006 | gas phase |
ΔrH° | 397.1 ± 5.1 | kcal/mol | G+TS | Kass, Filley, et al., 1986 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 396.5 ± 1.6 | kcal/mol | H-TS | Tian, Fattahi, et al., 2006 | gas phase |
ΔrG° | 389.0 ± 5.0 | kcal/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° | 13.7 ± 2.1 | kcal/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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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