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Cyclopropane,ethenyl-

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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
Deltafgas127.kJ/molChydRoth, Adamczak, et al., 1991 
Deltafgas131.2 ± 1.4kJ/molCcbLebedeva, 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
Deltafliquid102.5 ± 0.8kJ/molCcbLebedeva, Gutner, et al., 1977 
Quantity Value Units Method Reference Comment
Deltacliquid-3213.3 ± 0.8kJ/molCcbLebedeva, Gutner, et al., 1977Corresponding «DELTA»fliquid = 102.4 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-3233.kJ/molCmFierens and Nasielski, 1962Corresponding «DELTA»fliquid = 123. kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-3010.kJ/molCcbSlabey, 1952Corresponding «DELTA»fliquid = -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
Tboil313.6KN/AAnonymous, 1949Uncertainty assigned by TRC = 0.3 K; TRC
Tboil313.56KN/AVan Volkenburgh, Greenlee, et al., 1949Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tfus160.33KN/AAnonymous, 1949Uncertainty assigned by TRC = 0.3 K; TRC
Tfus160.7KN/AAnonymous, 1949Uncertainty assigned by TRC = 0.2 K; TRC
Tfus160.55KN/AVan Volkenburgh, Greenlee, et al., 1949Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Deltavap28.7 ± 1.3kJ/molVLebedeva, Gutner, et al., 1977ALS
Deltavap28.7kJ/molN/ALebedeva, Gutner, et al., 1977DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
28.9299.AStephenson and Malanowski, 1987Based on data from 289. - 310. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

1-vinylcyclopropanide anion + Hydrogen cation = Cyclopropane,ethenyl-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Deltar1647. ± 13.kJ/molG+TSGuo and Kass, 1992gas phase; Between Me2NH, H2O; B
Quantity Value Units Method Reference Comment
Deltar1617. ± 13.kJ/molIMRBGuo and Kass, 1992gas phase; Between Me2NH, H2O; B

2Hydrogen + Cyclopropane,ethenyl- = Pentane

By formula: 2H2 + C5H8 = C5H12

Quantity Value Units Method Reference Comment
Deltar-274. ± 0.8kJ/molChydRoth, Kirmse, et al., 1982liquid phase; solvent: Isooctane; ALS

Hydrogen + Cyclopropane,ethenyl- = Cyclopropane, ethyl-

By formula: H2 + C5H8 = C5H10

Quantity Value Units Method Reference Comment
Deltar-149. ± 4.2kJ/molChydChesick, 1963liquid phase; solvent: Acetic acid; ALS

Cyclopropane, methylmethylene- = Cyclopropane,ethenyl-

By formula: C5H8 = C5H8

Quantity Value Units Method Reference Comment
Deltar-2.4 ± 0.84kJ/molEqkChesick, 1963gas 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)816.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity787.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.7PEHarada, Seki, et al., 1973LLK
9.15PEBruckmann and Klessinger, 1974Vertical value; LLK
9.2PEGleiter, Heilbronner, et al., 1971Vertical value; LLK
9.1PEAskani, Gleiter, et al., 1971Vertical value; LLK

De-protonation reactions

1-vinylcyclopropanide anion + Hydrogen cation = Cyclopropane,ethenyl-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Deltar1647. ± 13.kJ/molG+TSGuo and Kass, 1992gas phase; Between Me2NH, H2O; B
Quantity Value Units Method Reference Comment
Deltar1617. ± 13.kJ/molIMRBGuo and Kass, 1992gas phase; Between Me2NH, H2O; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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]

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]

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 «pi»-systemen, Chem. Ber., 1974, 107, 1108. [all data]

Gleiter, Heilbronner, et al., 1971
Gleiter, R.; Heilbronner, E.; de Meijere, A., Die konjugative Wechselwirkung zwischen «pi»-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

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