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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
Deltafgas39.30kJ/molCmLacher, Walden, et al., 1950Heat of hydrobromination; ALS
Deltafgas53.30 ± 0.59kJ/molCmKnowlton and Rossini, 1949ALS
Quantity Value Units Method Reference Comment
Deltacgas-2091.4 ± 0.54kJ/molCmKnowlton and Rossini, 1949Corresponding «DELTA»fgas = 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.

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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil240. ± 3.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus146. ± 3.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple145.8KN/ATickner and Lossing, 1951Uncertainty assigned by TRC = 0.8 K; from change in slope of obs. vapor pressure; TRC
Ttriple145.57KN/ARuehrwein and Powell, 1946, 2Uncertainty assigned by TRC = 0.02 K; temp. scale for Tc = 273.10K; TRC
Ttriple145.59KN/ARuehrwein and Powell, 1946, 2Uncertainty assigned by TRC = 0.08 K; TRC
Quantity Value Units Method Reference Comment
Tc398.0 ± 0.3KN/ADaubert, 1996 
Tc398.3KN/ALin, Silberberg, et al., 1970Uncertainty assigned by TRC = 0.05 K; TRC
Tc397.80KN/ABooth and Morris, 1958Uncertainty assigned by TRC = 0.15 K; mean of measurements on three samples by visual obssrvation; TRC
Tc397.8KN/AHorneg, 1941Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Pc55.4 ± 0.5barN/ADaubert, 1996 
Pc55.7946barN/ALin, Silberberg, et al., 1970Uncertainty assigned by TRC = 0.0506 bar; TRC
Pc54.95barN/ABooth and Morris, 1958Uncertainty assigned by TRC = 0.2026 bar; mean of measurements on 3 samples, visual observation; TRC
Pc3.274barN/AHorneg, 1941Uncertainty assigned by TRC = 0.01 bar; TRC
Quantity Value Units Method Reference Comment
Vc0.162l/molN/ADaubert, 1996 
Quantity Value Units Method Reference Comment
rhoc6.15 ± 0.05mol/lN/ADaubert, 1996 
rhoc6.143mol/lN/ALin, Silberberg, et al., 1970Uncertainty assigned by TRC = 0.007 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap18.11kJ/molN/AMajer and Svoboda, 1985 
Deltavap17.02kJ/molN/ALin, Silberberg, et al., 1970, 2AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
20.054240.34N/ARuehrwein and Powell, 1946P = 101.325 kPa; DH
20.05240.3N/AMajer and Svoboda, 1985 
21.8210.N/ACalado, Filipe, et al., 1997Based on data from 195. - 225. K.; AC
20.4373.AStephenson and Malanowski, 1987Based on data from 358. - 398. K.; AC
19.9312.AStephenson and Malanowski, 1987Based on data from 297. - 359. K.; AC
20.3224.AStephenson and Malanowski, 1987Based on data from 188. - 239. K.; AC
19.9254.AStephenson and Malanowski, 1987Based on data from 239. - 298. K.; AC
21.1226.N/ARuehrwein and Powell, 1946, 3Based on data from 183. - 241. K. See also Boublik, Fried, et al., 1984.; AC

Entropy of vaporization

DeltavapS (J/mol*K) Temperature (K) Reference Comment
83.44240.34Ruehrwein and Powell, 1946P; DH

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
183.12 - 241.074.05015870.393-25.063Ruehrwein and Powell, 1946, 3Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
29.2145.BBondi, 1963AC
28.2128.A,MSTickner and Lossing, 1951, 2Based on data from 115. - 141. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
5.443145.57Ruehrwein and Powell, 1946DH
5.44145.6Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
37.39145.57Ruehrwein and Powell, 1946DH

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

C3H5- + Hydrogen cation = Cyclopropane

By formula: C3H5- + H+ = C3H6

Quantity Value Units Method Reference Comment
Deltar1716. ± 10.kJ/molAVGN/AAverage of 5 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltar1676. ± 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
Deltar-107.8 ± 1.3kJ/molCmLacher, Kianpour, et al., 1957gas phase; ALS
Deltar-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
Deltar77. ± 17.kJ/molEqkBenson and Amano, 1962gas phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.013 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species. Value at T = 294. K.
0.0111700.LN/A 

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
Deltar1716. ± 10.kJ/molAVGN/AAverage of 5 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltar1676. ± 10.kJ/molAVGN/AAverage of 3 out of 6 values; Individual data points

IR Spectrum

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Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

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

Spectrum

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Mass spectrum
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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 18855

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Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   D3h     Symmetry Number sigma = 6


 Sym.   No   Approximate   Selected Freq.  Infrared   Raman   Comments 
 Species   type of mode   Value   Rating   Value  Phase  Value  Phase

a1' 1 CH2 s-str 3038  C  ia 3038 S p gas
a1' 2 CH2 scis 1479  D  ia 1504 W p gas FR(2«nu»14)
a1' 2 CH2 scis 1479  D  ia 1453 W p gas FR(2«nu»14)
a1' 3 Ring str 1188  C  ia 1188 S p gas
a1 4 CH2 twist 1126  D 1126 ia VW gas 1133 ia gas
a2' 5 CH2 wag 1070  D 1075 ia sln.  ia OC(«nu»5+«nu»10)
a2 6 CH2 a-str 3103  C 3103 S gas  ia
a2 7 CH2 rock 854  C 854 S gas  ia
e' 8 CH2 s-str 3025  C 3025 VS gas 3020 VS p gas
e' 9 CH2 scis 1438  C 1438 M gas 1442 M dp gas
e' 10 CH2 wag 1029  C 1029 S gas 1023 VW liq.
e' 11 Ring deform 866  C 866 VS gas 866 S dp gas
e 12 CH2 a-str 3082  C  ia 3082 S dp gas
e 13 CH2 twist 1188  C  ia 1188 M dp gas
e 14 CH2 rock 739  C  ia 739 W dp gas

Source: Shimanouchi, 1972

Notes

VSVery strong
SStrong
MMedium
WWeak
VWVery weak
iaInactive
pPolarized
dpDepolarized
FRFermi resonance with an overtone or a combination tone indicated in the parentheses.
OCFrequency estimated from an overtone or a combination tone indicated in the parentheses.
C3~6 cm-1 uncertainty
D6~15 cm-1 uncertainty

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryBPX-530.356.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 «mu»m, H2
CapillaryBPX-530.357.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 «mu»m, H2
CapillaryCP Sil 5 CB20.348.8Do and Raulin, 199225. m/0.15 mm/2. «mu»m, H2
PackedSqualane27.344.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.345.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.346.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.347.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

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

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Column type Active phase I Reference Comment
PackedSE-30367.Peng, Ding, et al., 1988Supelcoport; 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
CapillaryOV-101331.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

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

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes331.Zenkevich, Chupalov, et al., 1996Program: not specified
PackedSE-30351.Robinson and Odell, 1971N2, 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
CapillaryDB-Wax405.Peng, Yang, et al., 1991Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, Site Links, NIST Free Links, 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]

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, 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, 1063-6. [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]

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]

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
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Notes

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