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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Information on this page:
Other data available:
Data at other public NIST sites:
- Microwave spectra (on physics lab web site)
- Gas Phase Kinetics Database
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Phase change data

Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_boil	240. ± 3.	K	AVG	N/A	Average of 8 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	146. ± 3.	K	AVG	N/A	Average of 6 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	145.8	K	N/A	Tickner and Lossing, 1951	Uncertainty assigned by TRC = 0.8 K; from change in slope of obs. vapor pressure; TRC
T_triple	145.57	K	N/A	Ruehrwein and Powell, 1946	Uncertainty assigned by TRC = 0.02 K; temp. scale for Tc = 273.10K; TRC
T_triple	145.59	K	N/A	Ruehrwein and Powell, 1946	Uncertainty assigned by TRC = 0.08 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	398.0 ± 0.3	K	N/A	Daubert, 1996
T_c	398.3	K	N/A	Lin, Silberberg, et al., 1970	Uncertainty assigned by TRC = 0.05 K; TRC
T_c	397.80	K	N/A	Booth and Morris, 1958	Uncertainty assigned by TRC = 0.15 K; mean of measurements on three samples by visual obssrvation; TRC
T_c	397.8	K	N/A	Horneg, 1941	Uncertainty assigned by TRC = 1. K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	54.7 ± 0.5	atm	N/A	Daubert, 1996
P_c	55.0650	atm	N/A	Lin, Silberberg, et al., 1970	Uncertainty assigned by TRC = 0.0499 atm; TRC
P_c	54.23	atm	N/A	Booth and Morris, 1958	Uncertainty assigned by TRC = 0.2000 atm; mean of measurements on 3 samples, visual observation; TRC
P_c	3.231	atm	N/A	Horneg, 1941	Uncertainty assigned by TRC = 0.01 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
V_c	0.162	l/mol	N/A	Daubert, 1996
Quantity	Value	Units	Method	Reference	Comment
ρ_c	6.15 ± 0.05	mol/l	N/A	Daubert, 1996
ρ_c	6.143	mol/l	N/A	Lin, Silberberg, et al., 1970	Uncertainty assigned by TRC = 0.007 mol/l; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	4.328	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	4.068	kcal/mol	N/A	Lin, Silberberg, et al., 1970, 2	AC

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
4.7930	240.34	N/A	Ruehrwein and Powell, 1946, 2	P = 101.325 kPa; DH
4.792	240.3	N/A	Majer and Svoboda, 1985
5.21	210.	N/A	Calado, Filipe, et al., 1997	Based on data from 195. to 225. K.; AC
4.88	373.	A	Stephenson and Malanowski, 1987	Based on data from 358. to 398. K.; AC
4.76	312.	A	Stephenson and Malanowski, 1987	Based on data from 297. to 359. K.; AC
4.85	224.	A	Stephenson and Malanowski, 1987	Based on data from 188. to 239. K.; AC
4.76	254.	A	Stephenson and Malanowski, 1987	Based on data from 239. to 298. K.; AC
5.04	226.	N/A	Ruehrwein and Powell, 1946, 3	Based on data from 183. to 241. K. See also Boublik, Fried, et al., 1984.; AC

Entropy of vaporization

Δ_vapS (cal/mol*K)	Temperature (K)	Reference	Comment
19.94	240.34	Ruehrwein and Powell, 1946, 2	P; DH

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
183.12 to 241.07	4.04444	870.393	-25.063	Ruehrwein and Powell, 1946, 3	Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
6.98	145.	B	Bondi, 1963	AC
6.74	128.	A,MS	Tickner and Lossing, 1951, 2	Based on data from 115. to 141. K.; AC

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
1.301	145.57	Ruehrwein and Powell, 1946, 2	DH
1.30	145.6	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
8.936	145.57	Ruehrwein and Powell, 1946, 2	DH

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:

Gas phase ion energetics data

Go To: Top, Phase change data, Gas Chromatography, References, Notes

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)	179.3	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	172.6	kcal/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°	410. ± 3.	kcal/mol	AVG	N/A	Average of 5 out of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	401. ± 3.	kcal/mol	AVG	N/A	Average of 3 out of 6 values; Individual data points

Gas Chromatography

Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	BPX-5	30.	356.	Aflalaye, Sternberg, et al., 1995	12. m/0.15 mm/0.25 μm, H2
Capillary	BPX-5	30.	357.	Aflalaye, Sternberg, et al., 1995	12. m/0.15 mm/0.25 μm, H2
Capillary	CP Sil 5 CB	20.	348.8	Do and Raulin, 1992	25. m/0.15 mm/2. μm, H2
Packed	Squalane	27.	344.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	49.	345.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	67.	346.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	86.	347.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Packed	SE-30	367.	Peng, Ding, et al., 1988	Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min)

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	OV-101	331.	Zenkevich, 2005	25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; T_start: 50. C; T_end: 250. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Polydimethyl siloxanes	331.	Zenkevich, Chupalov, et al., 1996	Program: not specified
Packed	SE-30	351.	Robinson and Odell, 1971	N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	405.	Peng, Yang, et al., 1991	Program: not specified

References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

Tickner and Lossing, 1951
Tickner, A.W.; Lossing, F.P., The Measurement of Low Vapor Pressures by Means of A Mass Spectrometer, J. Phys. Colloid Chem., 1951, 55, 733-40. [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, 1063-6. [all data]

Daubert, 1996
Daubert, T.E., Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes, J. Chem. Eng. Data, 1996, 41, 365-372. [all data]

Lin, Silberberg, et al., 1970
Lin, D.C.K.; Silberberg, I.H.; McKetta, J.J., Volumetric Behavior, Vapor Pressure and Critical Properties of Cyclopropane, J. Chem. Eng. Data, 1970, 15, 483. [all data]

Booth and Morris, 1958
Booth, H.S.; Morris, W.C., The Critical Constants and Vapor Pressure of Cyclopropane, J. Phys. Chem., 1958, 62, 875. [all data]

Horneg, 1941
Horneg, A.G., Personal Communication, A. G. Horneg, Ohio Chem. & Mfg. Co., Phys. Constants of the Principal Hydrocarbons, 1941. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Lin, Silberberg, et al., 1970, 2
Lin, David C.K.; Silberberg, I. Harold; McKetta, John J., Volumetric behavior, vapor pressures, and critical properties of cyclopropane, J. Chem. Eng. Data, 1970, 15, 4, 483-492, https://doi.org/10.1021/je60047a016 . [all data]

Ruehrwein and Powell, 1946, 2
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]

Calado, Filipe, et al., 1997
Calado, Jorge C.G.; Filipe, Eduardo J.M.; Lopes, José N.C., The vapour pressure of liquid cyclopropane, The Journal of Chemical Thermodynamics, 1997, 29, 12, 1435-1438, https://doi.org/10.1006/jcht.1997.0256 . [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]

Ruehrwein and Powell, 1946, 3
Ruehrwein, R.A.; Powell, T.M., The Heat Capacity, Vapor Pressure, Heats of Fusion and Vaporization of Cyclopropane. Entropy and Density of the Gas ¹, J. Am. Chem. Soc., 1946, 68, 6, 1063-1066, https://doi.org/10.1021/ja01210a044 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Bondi, 1963
Bondi, A., Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments., J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027 . [all data]

Tickner and Lossing, 1951, 2
Tickner, A.W.; Lossing, F.P., The Measurement of Low Vapor Pressures by Means of a Mass Spectrometer., J. Phys. Chem., 1951, 55, 5, 733-740, https://doi.org/10.1021/j150488a013 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Aflalaye, Sternberg, et al., 1995
Aflalaye, A.; Sternberg, R.; Raulin, F.; Vidal-Madjar, C., Gas chromatography of Titan's atmosphere. VI. Analysis of low-molecular-mass hydrocarbons and nitriles with BPX5 capillary columns, J. Chromatogr. A, 1995, 708, 2, 283-291, https://doi.org/10.1016/0021-9673(95)00410-O . [all data]

Do and Raulin, 1992
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column, J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Zenkevich, Chupalov, et al., 1996
Zenkevich, I.G.; Chupalov, A.A.; Herzschuh, R., Correlation of the Increments of Gas Chromatographic Retention Indices with the Differences of Innermolecular Energies of Reagents and Products of Chemical Reactions, Zh. Org. Khim. (Rus.), 1996, 32, 11, 1685-1691. [all data]

Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L., A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices, J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

Symbols used in this document:

AE	Appearance energy
IE (evaluated)	Recommended ionization energy
P_c	Critical pressure
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
V_c	Critical volume
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_subH	Enthalpy of sublimation
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions
Δ_vapS	Entropy of vaporization
ρ_c	Critical density

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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