Cyclopropane,ethenyl-
- Formula: C5H8
- Molecular weight: 68.1170
- 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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 127. | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | |
ΔfH°gas | 131.2 ± 1.4 | kJ/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 | 102.5 ± 0.8 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1977 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3213.3 ± 0.8 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1977 | Corresponding ΔfHºliquid = 102.4 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -3233. | kJ/mol | Cm | Fierens and Nasielski, 1962 | Corresponding ΔfHºliquid = 123. kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -3010. | kJ/mol | Ccb | Slabey, 1952 | Corresponding ΔfHºliquid = -100. kJ/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° | 28.7 ± 1.3 | kJ/mol | V | Lebedeva, Gutner, et al., 1977 | ALS |
ΔvapH° | 28.7 | kJ/mol | N/A | Lebedeva, Gutner, et al., 1977 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
28.9 | 299. | A | Stephenson and Malanowski, 1987 | Based on data from 289. to 310. K.; AC |
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
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C5H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 816.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 787.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.7 | PE | Harada, Seki, et al., 1973 | LLK |
9.15 | PE | Bruckmann and Klessinger, 1974 | Vertical value; LLK |
9.2 | PE | Gleiter, Heilbronner, et al., 1971 | Vertical value; LLK |
9.1 | PE | Askani, Gleiter, et al., 1971 | Vertical value; LLK |
De-protonation reactions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1647. ± 13. | kJ/mol | G+TS | Guo and Kass, 1992 | gas phase; Between Me2NH, H2O; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1617. ± 13. | kJ/mol | IMRB | Guo and Kass, 1992 | gas phase; Between Me2NH, H2O; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]
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]
Harada, Seki, et al., 1973
Harada, Y.; Seki, K.; Suzuki, A.; Inokuchi, H.,
Photoelectron spectrum of vinylcyclopropane,
Chem. Lett., 1973, 893. [all data]
Bruckmann and Klessinger, 1974
Bruckmann, P.; Klessinger, M.,
Photoelektronenspektren organischer verbindungen. V. Wechselwirkung kleiner ringe mit π-systemen,
Chem. Ber., 1974, 107, 1108. [all data]
Gleiter, Heilbronner, et al., 1971
Gleiter, R.; Heilbronner, E.; de Meijere, A.,
Die konjugative Wechselwirkung zwischen π-und Walsh-Orbitalen: das Photoelektron-Spektrum des Homofulvens,
Helv. Chim. Acta, 1971, 54, 1029. [all data]
Askani, Gleiter, et al., 1971
Askani, R.; Gleiter, R.; Heilbronner, E.; Hornung, V.; Musso, H.,
The orbital sequence in semibullvalene, barbaralene and dihydrobullvalene,
Tetrahedron Lett., 1971, 4461. [all data]
Guo and Kass, 1992
Guo, H.Z.; Kass, S.R.,
Vinylcyclopropyl Anion - Structure, Reactivity, Thermodynamic Properties, and an Unusual Rearrangement,
J. Am. Chem. Soc., 1992, 114, 4, 1244, https://doi.org/10.1021/ja00030a019
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction 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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