Cyclopropane,ethenyl-
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChI: InChI=1S/C5H8/c1-2-5-3-4-5/h2,5H,1,3-4H2
- IUPAC Standard InChIKey: YIWFBNMYFYINAD-UHFFFAOYSA-N
- CAS Registry Number: 693-86-7
- 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: Ethenylcyclopropane
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 30.4 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | |
| ΔfH°gas | 31.36 ± 0.33 | kcal/mol | Ccb | Lebedeva, Gutner, et al., 1977 |
Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 24.5 ± 0.2 | kcal/mol | Ccb | Lebedeva, Gutner, et al., 1977 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -768.0 ± 0.2 | kcal/mol | Ccb | Lebedeva, Gutner, et al., 1977 | Corresponding ΔfHºliquid = 24.47 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -772.8 | kcal/mol | Cm | Fierens and Nasielski, 1962 | Corresponding ΔfHºliquid = 29.3 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -720. | kcal/mol | Ccb | Slabey, 1952 | Corresponding ΔfHºliquid = -24. kcal/mol (simple calculation by NIST; no Washburn corrections) |
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 313.6 | K | N/A | Anonymous, 1949 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Tboil | 313.56 | K | N/A | Van Volkenburgh, Greenlee, et al., 1949 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 160.33 | K | N/A | Anonymous, 1949 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Tfus | 160.7 | K | N/A | Anonymous, 1949 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Tfus | 160.55 | K | N/A | Van Volkenburgh, Greenlee, et al., 1949 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 6.86 ± 0.31 | kcal/mol | V | Lebedeva, Gutner, et al., 1977 | ALS |
| ΔvapH° | 6.86 | kcal/mol | N/A | Lebedeva, Gutner, et al., 1977 | DRB |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 6.91 | 299. | A | Stephenson and Malanowski, 1987 | Based on data from 289. to 310. K.; AC |
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 | OV-1 | 30. | 536. | Heberger, 1990 | 25. m/0.25 mm/0.50 μm, He |
| Capillary | Squalane | 120. | 515.6 | Schomburg and Dielmann, 1973 | Column length: 100. m; Column diameter: 0.25 mm |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Lebedeva, Gutner, et al., 1977
Lebedeva, N.D.; Gutner, N.M.; Nazarova, L.F.,
Enthalpies of burning and the formation of some substituted derivatives of cyclopropane,
Termodin. Org. Soedin., 1977, 26-29. [all data]
Fierens and Nasielski, 1962
Fierens, P.J.C.; Nasielski, J.,
Chaleurs de combustion de derives cyclopropaniques et pouvoir de conjugaison du groupe cyclopropyle,
Bull. Soc. Chim. Belg., 1962, 71, 187-202. [all data]
Slabey, 1952
Slabey, V.A.,
Dehydration of methylcyclopropylcarbinol over alumina. A synthesis of vinylcyclopropane,
J. Am. Chem. Soc., 1952, 74, 4930-4932. [all data]
Anonymous, 1949
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1949. [all data]
Van Volkenburgh, Greenlee, et al., 1949
Van Volkenburgh, R.; Greenlee, K.W.; Derfer, J.M.; Boord, C.E.,
A Synthesis of Vinylcyclopropane,
J. Am. Chem. Soc., 1949, 71, 3595. [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]
Heberger, 1990
Heberger, K.,
Identification of C5H8 Isomers Through Reactions of Singlet Methylene, CH2(ã1A1), with Unsaturated Hydrocarbons Using Capillary Gas Chromatography - Mass Spectrometry,
Analyst, 1990, 115, 6, 725-729, https://doi.org/10.1039/an9901500725
. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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