Cyclopropane

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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 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
Δfgas39.30kJ/molCmLacher, Walden, et al., 1950Heat of hydrobromination; ALS
Δfgas53.30 ± 0.59kJ/molCmKnowlton and Rossini, 1949ALS
Quantity Value Units Method Reference Comment
Δcgas-2091.4 ± 0.54kJ/molCmKnowlton and Rossini, 1949Corresponding Δfgas = 53.35 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
33.2650.Dorofeeva O.V., 1986Selected S(T) and Cp(T) values are in good agreement with those calculated earlier [ Kobe K.A., 1950]. The agreement with the data of [80KAR/PAM] increases as the temperature increases (up to 2 J/mol*K in Cp(1000 K)).; GT
33.32100.
34.56150.
38.91200.
50.69273.15
55.6 ± 1.0298.15
55.94300.
76.05400.
93.86500.
108.54600.
120.68700.
130.91800.
139.66900.
147.211000.
153.751100.
159.431200.
164.381300.
168.691400.
172.451500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
35.38157.8Kistiakowsky G.B., 1940Please also see Kistiakowsky G.B., 1940, 2.; GT
42.16220.1
42.55223.7
48.68258.7
50.63272.15
54.66291.4
55.25295.5
56.48300.48
59.29313.9
59.27316.7
60.90325.1
62.17332.8
63.18333.70
64.27338.9
63.26339.6
70.17368.46

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: Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
liquid142.63J/mol*KN/ARuehrwein and Powell, 1946 

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
81.34240.Ruehrwein and Powell, 1946T = 14 to 240 K.

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

C3H5- + Hydrogen cation = Cyclopropane

By formula: C3H5- + H+ = C3H6

Quantity Value Units Method Reference Comment
Δr1716. ± 10.kJ/molAVGN/AAverage of 5 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δr1676. ± 10.kJ/molAVGN/AAverage of 3 out of 6 values; Individual data points

Hydrogen bromide + Cyclopropane = Propane, 1-bromo-

By formula: HBr + C3H6 = C3H7Br

Quantity Value Units Method Reference Comment
Δr-107.8 ± 1.3kJ/molCmLacher, Kianpour, et al., 1957gas phase; ALS
Δr-94.94 ± 0.65kJ/molCmLacher, Walden, et al., 1950gas phase; Heat of hydrobromination; ALS

Propane, 1,3-diiodo- = Cyclopropane + Iodine

By formula: C3H6I2 = C3H6 + I2

Quantity Value Units Method Reference Comment
Δr77. ± 17.kJ/molEqkBenson and Amano, 1962gas 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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C3H6+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.86 ± 0.04eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)750.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity722.2kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.90PITraeger, 1984LBLHLM
9.86EQLias and Buckley, 1984LBLHLM
10.60PEKimura, Katsumata, et al., 1981LLK
9.8 ± 0.1PEBieri, Burger, et al., 1977LLK
10.3 ± 0.1EIRothgery, Holt, et al., 1975LLK
9.91 ± 0.03PIKrassig, Reinke, et al., 1974LLK
≤9.93EILossing, 1972LLK
≤9.8PEBasch, Robin, et al., 1969RDSH
10.1CICermak, 1968RDSH
10.06 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
10.54PEPlemenkov, Villem, et al., 1981Vertical value; LLK
10.6 ± 0.1PEBieri, Burger, et al., 1977Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2+19.3C2H4EIHaney and Franklin, 1968RDSH
C2H2+12.71 ± 0.06CH4PIKrassig, Reinke, et al., 1974LLK
C2H2+13.1CH4EIHaney and Franklin, 1968RDSH
C2H3+12.64 ± 0.05CH3PIKrassig, Reinke, et al., 1974LLK
C2H3+13.4CH3EIHaney and Franklin, 1968RDSH
C2H3+13.3 ± 0.2CH3EIHarrison and Tait, 1962RDSH
C3H+19.7 ± 0.52H2+HEIHarrison and Tait, 1962RDSH
C3H3+12.1 ± 0.1H2+H(-)PIKrassig, Reinke, et al., 1974LLK
C3H3+12.9 ± 0.1H2+HPIKrassig, Reinke, et al., 1974LLK
C3H3+13.7 ± 0.1H2+HEIHarrison and Tait, 1962RDSH
C3H4+11.64 ± 0.15H2PIKrassig, Reinke, et al., 1974LLK
C3H4+11.6 ± 0.1H2EIHarrison and Tait, 1962RDSH
C3H5+11.43HPITraeger, 1984LBLHLM
C3H5+11.47HPIButtrill, Williamson, et al., 1975LLK
C3H5+10.74 ± 0.09H(-)PIKrassig, Reinke, et al., 1974LLK
C3H5+11.44 ± 0.05HPIKrassig, Reinke, et al., 1974LLK
C3H5+11.49HEILossing, 1972LLK

De-protonation reactions

C3H5- + Hydrogen cation = Cyclopropane

By formula: C3H5- + H+ = C3H6

Quantity Value Units Method Reference Comment
Δr1716. ± 10.kJ/molAVGN/AAverage of 5 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δr1676. ± 10.kJ/molAVGN/AAverage of 3 out of 6 values; Individual data points

References

Go To: Top, Gas phase thermochemistry data, Condensed 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.

Lacher, Walden, et al., 1950
Lacher, J.R.; Walden, C.H.; Lea, K.R.; Park, J.D., Vapor phase heats of hydrobromination of cyclopropane and propylene, J. Am. Chem. Soc., 1950, 72, 331-333. [all data]

Knowlton and Rossini, 1949
Knowlton, J.W.; Rossini, F.D., Heats of combustion and formation of cyclopropane, J. Res. NBS, 1949, 43, 113-115. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Kobe K.A., 1950
Kobe K.A., Thermochemistry for the petrochemical industry. XIV. Some miscellaneous hydrocarbons, Petrol. Refiner, 1950, 29 (12), 93-96. [all data]

Kistiakowsky G.B., 1940
Kistiakowsky G.B., Gaseous heat capacities. II, J. Chem. Phys., 1940, 8, 610-618. [all data]

Kistiakowsky G.B., 1940, 2
Kistiakowsky G.B., The low temperature gaseous heat capacities of certain C3 hydrocarbons, J. Chem. Phys., 1940, 8, 970-977. [all data]

Ruehrwein and Powell, 1946
Ruehrwein, R.A.; Powell, T.M., The heat capacity, vapor pressure, heats of fusion and vaporization of cyclopropane. Entropy and density of the gas, J. Am. Chem. Soc., 1946, 68, 1063-1068. [all data]

Lacher, Kianpour, et al., 1957
Lacher, J.R.; Kianpour, A.; Park, J.D., Reaction heats of organic halogen compounds. X. Vapor phase heats of hydrobromination of cyclopropane and propylene, J. Phys. Chem., 1957, 61, 1124-1125. [all data]

Benson and Amano, 1962
Benson, S.W.; Amano, A., Thermodynamics of iodine addition to ethylene, propylene, and cyclopropane, J. Chem. Phys., 1962, 36, 3464-3471. [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]

Traeger, 1984
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [all data]

Lias and Buckley, 1984
Lias, S.G.; Buckley, T.J., Structures and reactions of C3H6+ ions generated in cyclopropane, Int. J. Mass Spectrom. Ion Processes, 1984, 56, 123. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [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]

Rothgery, Holt, et al., 1975
Rothgery, E.F.; Holt, J.; McGee, H.A., Jr., Cryochemical synthesis and molecular energetics of cyclopropanone and some related compounds, J. Am. Chem. Soc., 1975, 97, 4971. [all data]

Krassig, Reinke, et al., 1974
Krassig, R.; Reinke, D.; Baumgartel, H., Photo-reaktionen kleiner organischer molekule II. Die photoionenspektren der Isomeren propylen-cyclopropan und acetaldehyd-athylenoxyd, Ber. Bunsen-Ges. Phys. Chem., 1974, 78, 425. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions, Can. J. Chem., 1972, 50, 3973. [all data]

Basch, Robin, et al., 1969
Basch, H.; Robin, M.B.; Kuebler, N.A.; Baker, C.; Turner, D.W., Optical and photoelectron spectra of small rings. III. The saturated three-membered rings, J. Chem. Phys., 1969, 51, 52. [all data]

Cermak, 1968
Cermak, V., Penning ionization electron spectroscopy. I. Determination of ionization potentials of polyatomic molecules, Collection Czech. Chem. Commun., 1968, 33, 2739. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Plemenkov, Villem, et al., 1981
Plemenkov, V.V.; Villem, Y.Y.; Villem, N.V.; Bolesov, I.G.; Surmina, L.S.; Yakushkina, N.I.; Formanovskii, A.A., Photoelectron spectra of polyalkylcyclopropenes and polyalkylcyclopropanes, Zh. Obshch. Khim., 1981, 51, 2076. [all data]

Haney and Franklin, 1968
Haney, M.A.; Franklin, J.L., Correlation of excess energies of electron-impact dissociations with the translational energies of the products, J.Chem. Phys., 1968, 48, 4093. [all data]

Harrison and Tait, 1962
Harrison, A.G.; Tait, J.M.S., Concurrent ion-molecule reactions leading to the same product ion, Can. J. Chem., 1962, 40, 1986. [all data]

Buttrill, Williamson, et al., 1975
Buttrill, S.E., Jr.; Williamson, A.D.; LeBreton, P., Photoionization measurement of the heat of formation of allyl cations, J. Chem. Phys., 1975, 62, 1586. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References