Methylenecyclopropane
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChIKey: XSGHLZBESSREDT-UHFFFAOYSA-N
- CAS Registry Number: 6142-73-0
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Cyclopropane, methylene-
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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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 | 201. ± 2. | kJ/mol | Cm | Wiberg and Fenoglio, 1968 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -2632.0 ± 1.9 | kJ/mol | Cm | Wiberg and Fenoglio, 1968 | Corresponding ΔfHºgas = 200.5 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 |
---|---|---|---|
72.93 | 298.15 | Yursha I.A., 1974 | Please also see Kabo G.Y., 1973.; GT |
73.35 | 300. | ||
95.60 | 400. | ||
115.14 | 500. | ||
130.29 | 600. | ||
142.84 | 700. | ||
153.55 | 800. | ||
162.72 | 900. | ||
170.54 | 1000. |
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 by: Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 134.5 | K | N/A | Gragson, Greenlee, et al., 1953 | Uncertainty assigned by TRC = 1. K |
Tfus | 137. | K | N/A | Gragson, Greenlee, et al., 1953 | Uncertainty assigned by TRC = 1. K |
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 compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C4H6+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.6 ± 0.1 | PE | Bieri, Burger, et al., 1977 | Vertical value |
9.57 | PE | Wiberg, Ellison, et al., 1976 | Vertical value |
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 | 161511 |
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 |
---|---|---|---|---|---|
Capillary | Squalane | 120. | 432.5 | Schomburg and Dielmann, 1973 | Column length: 100. m; Column diameter: 0.25 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 432. | Chen, 2008 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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]
Yursha I.A., 1974
Yursha I.A.,
Equilibriums and thermodynamics of isomerization of methylcyclohexenes,
Neftekhimiya, 1974, 14, 688-693. [all data]
Kabo G.Y., 1973
Kabo G.Y.,
Thermodynamic properties of some hydrocarbons containing three-membered rings,
Vestn. Beloruss. Univ., Ser. 2, 1973, 3-6. [all data]
Gragson, Greenlee, et al., 1953
Gragson, J.T.; Greenlee, K.W.; Derfer, J.M.; Boord, C.E.,
J. Am. Chem. Soc., 1953, 75, 3344-7. [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]
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]
Schomburg and Dielmann, 1973
Schomburg, G.; Dielmann, G.,
Use of retention increments for identification and correlation of saturated and unsaturated cyclopropane hydrocarbons by means of Kovats indices,
Anal. Chem., 1973, 45, 9, 1647-1658, https://doi.org/10.1021/ac60331a021
. [all data]
Chen, 2008
Chen, H.-F.,
Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression,
Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003
. [all data]
Notes
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- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Tfus Fusion (melting) point ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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