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
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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 |
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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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° | 393.6 ± 3.1 | kcal/mol | G+TS | Guo and Kass, 1992 | gas phase; Between Me2NH, H2O; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 386.5 ± 3.0 | kcal/mol | IMRB | Guo and Kass, 1992 | gas phase; Between Me2NH, H2O; B |
By formula: 2H2 + C5H8 = C5H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -65.5 ± 0.2 | kcal/mol | Chyd | Roth, Kirmse, et al., 1982 | liquid phase; solvent: Isooctane; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -35.5 ± 1.0 | kcal/mol | Chyd | Chesick, 1963 | liquid phase; solvent: Acetic acid; ALS |
By formula: C5H8 = C5H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.57 ± 0.20 | kcal/mol | Eqk | Chesick, 1963 | gas phase; ALS |
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) | 195.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 188.2 | kcal/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° | 393.6 ± 3.1 | kcal/mol | G+TS | Guo and Kass, 1992 | gas phase; Between Me2NH, H2O; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 386.5 ± 3.0 | kcal/mol | IMRB | Guo and Kass, 1992 | gas phase; Between Me2NH, H2O; B |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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]
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]
Roth, Kirmse, et al., 1982
Roth, W.R.; Kirmse, W.; Hoffmann, W.; Lennartz, H.W.,
Heats of hydrogenation. III. Effect of fluoro substituents on the thermal rearrangement of cyclopropane systems,
Chem. Ber., 1982, 115, 2508-2515. [all data]
Chesick, 1963
Chesick, J.P.,
Kinetics of the thermal interconversion of 2-methylmethylenecyclopropane and ethylidenecyclopropane,
J. Am. Chem. Soc., 1963, 85, 2720-2723. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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