Cyclopropane

Formula: C₃H₆
Molecular weight: 42.0797
IUPAC Standard InChI: InChI=1S/C3H6/c1-2-3-1/h1-3H2
IUPAC Standard InChIKey: LVZWSLJZHVFIQJ-UHFFFAOYSA-N
CAS Registry Number: 75-19-4
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: Trimethylene; Trimethylene (cyclic); UN 1027; Cyclopropnane
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Gas phase thermochemistry data

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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
Δ_fH°_gas	39.30	kJ/mol	Cm	Lacher, Walden, et al., 1950	Heat of hydrobromination; ALS
Δ_fH°_gas	53.30 ± 0.59	kJ/mol	Cm	Knowlton and Rossini, 1949	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-2091.4 ± 0.54	kJ/mol	Cm	Knowlton and Rossini, 1949	Corresponding Δ_fHº_gas = 53.35 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
33.26	50.	Dorofeeva O.V., 1986	Selected 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
33.32	100.
34.56	150.
38.91	200.
50.69	273.15
55.6 ± 1.0	298.15
55.94	300.
76.05	400.
93.86	500.
108.54	600.
120.68	700.
130.91	800.
139.66	900.
147.21	1000.
153.75	1100.
159.43	1200.
164.38	1300.
168.69	1400.
172.45	1500.

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
35.38	157.8	Kistiakowsky G.B., 1940	Please also see Kistiakowsky G.B., 1940, 2.; GT
42.16	220.1
42.55	223.7
48.68	258.7
50.63	272.15
54.66	291.4
55.25	295.5
56.48	300.48
59.29	313.9
59.27	316.7
60.90	325.1
62.17	332.8
63.18	333.70
64.27	338.9
63.26	339.6
70.17	368.46

Reaction thermochemistry data

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Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C₃H₅^- + = Cyclopropane

By formula: C₃H₅^- + H⁺ = C₃H₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1716. ± 10.	kJ/mol	AVG	N/A	Average of 5 out of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1676. ± 10.	kJ/mol	AVG	N/A	Average of 3 out of 6 values; Individual data points

+ Cyclopropane =

By formula: HBr + C₃H₆ = C₃H₇Br

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

= Cyclopropane +

By formula: C₃H₆I₂ = C₃H₆ + I₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	77. ± 17.	kJ/mol	Eqk	Benson and Amano, 1962	gas phase; ALS

Gas phase ion energetics data

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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 ± 0.04	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	750.3	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	722.2	kJ/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.90	PI	Traeger, 1984	LBLHLM
9.86	EQ	Lias and Buckley, 1984	LBLHLM
10.60	PE	Kimura, Katsumata, et al., 1981	LLK
9.8 ± 0.1	PE	Bieri, Burger, et al., 1977	LLK
10.3 ± 0.1	EI	Rothgery, Holt, et al., 1975	LLK
9.91 ± 0.03	PI	Krassig, Reinke, et al., 1974	LLK
≤9.93	EI	Lossing, 1972	LLK
≤9.8	PE	Basch, Robin, et al., 1969	RDSH
10.1	CI	Cermak, 1968	RDSH
10.06 ± 0.03	PI	Watanabe, Nakayama, et al., 1962	RDSH
10.54	PE	Plemenkov, Villem, et al., 1981	Vertical value; LLK
10.6 ± 0.1	PE	Bieri, Burger, et al., 1977	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH₂⁺	19.3	C₂H₄	EI	Haney and Franklin, 1968	RDSH
C₂H₂⁺	12.71 ± 0.06	CH₄	PI	Krassig, Reinke, et al., 1974	LLK
C₂H₂⁺	13.1	CH₄	EI	Haney and Franklin, 1968	RDSH
C₂H₃⁺	12.64 ± 0.05	CH₃	PI	Krassig, Reinke, et al., 1974	LLK
C₂H₃⁺	13.4	CH₃	EI	Haney and Franklin, 1968	RDSH
C₂H₃⁺	13.3 ± 0.2	CH₃	EI	Harrison and Tait, 1962	RDSH
C₃H⁺	19.7 ± 0.5	2H₂+H	EI	Harrison and Tait, 1962	RDSH
C₃H₃⁺	12.1 ± 0.1	H₂+H(^-)	PI	Krassig, Reinke, et al., 1974	LLK
C₃H₃⁺	12.9 ± 0.1	H₂+H	PI	Krassig, Reinke, et al., 1974	LLK
C₃H₃⁺	13.7 ± 0.1	H₂+H	EI	Harrison and Tait, 1962	RDSH
C₃H₄⁺	11.64 ± 0.15	H₂	PI	Krassig, Reinke, et al., 1974	LLK
C₃H₄⁺	11.6 ± 0.1	H₂	EI	Harrison and Tait, 1962	RDSH
C₃H₅⁺	11.43	H	PI	Traeger, 1984	LBLHLM
C₃H₅⁺	11.47	H	PI	Buttrill, Williamson, et al., 1975	LLK
C₃H₅⁺	10.74 ± 0.09	H(^-)	PI	Krassig, Reinke, et al., 1974	LLK
C₃H₅⁺	11.44 ± 0.05	H	PI	Krassig, Reinke, et al., 1974	LLK
C₃H₅⁺	11.49	H	EI	Lossing, 1972	LLK

De-protonation reactions

C₃H₅^- + = Cyclopropane

By formula: C₃H₅^- + H⁺ = C₃H₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1716. ± 10.	kJ/mol	AVG	N/A	Average of 5 out of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1676. ± 10.	kJ/mol	AVG	N/A	Average of 3 out of 6 values; Individual data points

References

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

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]

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, Reaction thermochemistry data, Gas phase ion energetics data, References

Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
IE (evaluated)	Recommended ionization energy
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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