Propyne

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Gas phase thermochemistry data

Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, References, Notes

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
Δfgas44.32 ± 0.21kcal/molCcbWagman, Kilpatrick, et al., 1945Unpublished work of E. J. Prosen; ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
7.97650.Thermodynamics Research Center, 1997p=1 bar. Recommended values are in good agreement with other statistically calculated values [ Wagman D.D., 1945, Daykin P.N., 1962].; GT
8.769100.
10.14150.
11.61200.
13.78273.15
14.51298.15
14.57300.
17.34400.
19.74500.
21.80600.
23.59700.
25.148800.
26.520900.
27.7271000.
28.7831100.
29.7111200.
30.5211300.
31.2311400.
31.8551500.

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
13.76272.28Kistiakowsky G.B., 1940Other experimental values of heat capacity [ Kistiakowsky G.B., 1940, 2] were measured with large uncertainties.; GT
14.58299.59
15.56332.83
16.52369.21

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, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil250.0 ± 0.5KAVGN/AAverage of 18 out of 19 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus170.2 ± 0.6KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple168.5KN/AMaass and Wright, 1921Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc402.4 ± 0.2KN/ATsonopoulos and Ambrose, 1996 
Tc402.38KN/AVohra, Kang, et al., 1962Uncertainty assigned by TRC = 0.05 K; TRC
Tc401.1KN/AMaass and Wright, 1921Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Pc55.6 ± 0.2atmN/ATsonopoulos and Ambrose, 1996 
Pc55.5400atmN/AVohra, Kang, et al., 1962Uncertainty assigned by TRC = 0.0499 atm; TRC
Quantity Value Units Method Reference Comment
Vc0.1635l/molN/ATsonopoulos and Ambrose, 1996 
Quantity Value Units Method Reference Comment
ρc6.12 ± 0.02mol/lN/ATsonopoulos and Ambrose, 1996 
ρc6.113mol/lN/AVohra, Kang, et al., 1962Uncertainty assigned by TRC = 0.01 mol/l; TRC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
5.50242.AStephenson and Malanowski, 1987Based on data from 183. to 257. K.; AC
4.97272.AStephenson and Malanowski, 1987Based on data from 257. to 402. K.; AC
5.07318.AStephenson and Malanowski, 1987Based on data from 303. to 361. K.; AC
5.23374.AStephenson and Malanowski, 1987Based on data from 359. to 402. K.; AC
5.54264.AStephenson and Malanowski, 1987Based on data from 249. to 306. K.; AC
5.28275.N/AReid, 1972AC
5.71240.N/AVan Hook, 1967Based on data from 162. to 255. K.; AC
5.16338.N/AVohra, Kang, et al., 1962Based on data from 323. to 400. K.; AC
5.59235.N/ABooth, Burchfield, et al., 1933Based on data from 194. to 250. K. See also Boublik, Fried, et al., 1984.; AC
5.11230.N/AMaass and Wright, 1921Based on data from 200. to 260. K.; AC

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
161.5 to 254.274.946481226.123-1.926van Hook, 1967Coefficents calculated by NIST from author's data.
249.9 to 398.4.02498818.384-46.457Stull, 1947Coefficents calculated by NIST from author's data.

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:


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
0.093 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.091 LN/A 
0.092 VN/A 

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change data, Henry's Law data, References, Notes

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
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 C3H4+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.36 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)179.kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity172.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.37PEKimura, Katsumata, et al., 1981LLK
10.37 ± 0.01PIParr, Jason, et al., 1979LLK
10.38 ± 0.01TEParr, Jason, et al., 1979LLK
10.37 ± 0.02PEBieri, Burger, et al., 1977LLK
10.364 ± 0.005PECarlier, Dubois, et al., 1975LLK
10.37PEBrogli, Heilbronner, et al., 1973LLK
10.36EILossing, 1972LLK
10.365 ± 0.015PIPerson and Nicole, 1970RDSH
10.37PEFrost, Herring, et al., 1970RDSH
10.349 ± 0.015PIOmura, Kaneko, et al., 1969RDSH
10.36 ± 0.02PIMatthews and Warneck, 1969RDSH
10.38 ± 0.02PIParr and Elder, 1968RDSH
10.37 ± 0.01PEBaker and Turner, 1968RDSH
10.5 ± 0.1EIGil'burd, Syrvatka, et al., 1967RDSH
10.36SWatanabe and Namioka, 1956RDSH
10.36 ± 0.01PIWatanabe and Namioka, 1956RDSH
10.37PEKimura, Katsumata, et al., 1981Vertical value; LLK
10.54PEBieri and Asbrink, 1980Vertical value; LLK
10.36PEAndreocci, Bitchev, et al., 1979Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+16.0C2HEISenSharma and Franklin, 1973LLK
CH3+14.6 ± 0.1C2HEIGil'burd, Syrvatka, et al., 1967RDSH
CH3+15.4 ± 0.5?EICoats and Anderson, 1957RDSH
C2H+17.2 ± 0.5CH3EICoats and Anderson, 1957RDSH
C2H2+15.2 ± 0.1CH2EIGil'burd, Syrvatka, et al., 1967RDSH
C3+26. ± 1.?EICoats and Anderson, 1957RDSH
C3H+17.12 ± 0.06H+H2PIParr, Jason, et al., 1979LLK
C3H+16.6 ± 0.02H+H2TEParr, Jason, et al., 1979LLK
C3H+14.0 ± 0.1H2+HEIGil'burd, Syrvatka, et al., 1967RDSH
C3H+17.5 ± 0.5H2+HEIHarrison and Tait, 1962RDSH
C3H+15.4 ± 0.3H2+HEICoats and Anderson, 1957RDSH
C3H2+13.68 ± 0.04H2PIParr, Jason, et al., 1979LLK
C3H2+13.0 ± 0.1H2TEParr, Jason, et al., 1979LLK
C3H2+13.8 ± 0.1H2EIGil'burd, Syrvatka, et al., 1967RDSH
C3H2+14.0 ± 0.1H2EICoats and Anderson, 1957RDSH
C3H3+11.2 ± 0.1HTEParr, Jason, et al., 1979LLK
C3H3+11.58 ± 0.04HPIParr, Jason, et al., 1979LLK
C3H3+11.60HEILossing, 1972LLK
C3H3+11.56 ± 0.03HPIMatthews and Warneck, 1969RDSH
C3H3+11.55 ± 0.02HPIParr and Elder, 1968RDSH
C3H3+11.9 ± 0.1HEIGil'burd, Syrvatka, et al., 1967RDSH

De-protonation reactions

C3H3- + Hydrogen cation = Propyne

By formula: C3H3- + H+ = C3H4

Quantity Value Units Method Reference Comment
Δr380.3 ± 2.1kcal/molG+TSGal, Decouzon, et al., 2001gas phase; B
Δr381.8 ± 2.3kcal/molD-EARobinson, Polak, et al., 1995gas phase; B
Δr381.1 ± 2.1kcal/molG+TSRobinson, Polak, et al., 1995gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B
Δr381.0 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr372.6 ± 2.0kcal/molIMREGal, Decouzon, et al., 2001gas phase; B
Δr373.4 ± 2.0kcal/molIMRERobinson, Polak, et al., 1995gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B
Δr373.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Henry's Law 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.

Wagman, Kilpatrick, et al., 1945
Wagman, D.D.; Kilpatrick, J.E.; Pitzer, K.S.; Rossini, F.D., Heats, equilibrium constants, and free energies of formation of the acetylene hydrocarbons through the pentynes, to 1,500° K, J. Res. NBS, 1945, 35, 467-496. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Wagman D.D., 1945
Wagman D.D., Heats, equilibrium constants, and free energies of formation of the acetylene hydrocarbons through the pentynes to 1500 K, J. Res. Nat. Bur. Stand., 1945, 35, 467-496. [all data]

Daykin P.N., 1962
Daykin P.N., Potential energy constants, rotational distortion constants, and thermodynamic properties of methylacetylenes, J. Chem. Phys., 1962, 37, 1087-1094. [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]

Maass and Wright, 1921
Maass, O.; Wright, C.H., SOME PHYSICAL PROPERTIES OF HYDROCARBONS CONTAINING TWO AND THREE CARBON ATOMS., J. Am. Chem. Soc., 1921, 43, 5, 1098-1111, https://doi.org/10.1021/ja01438a013 . [all data]

Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons, J. Chem. Eng. Data, 1996, 41, 645-656. [all data]

Vohra, Kang, et al., 1962
Vohra, S.P.; Kang, T.L.; Kobe, K.A.; McKetta, J.J., P-V-T Properties of Propyne., J. Chem. Eng. Data, 1962, 7, 1, 150-155, https://doi.org/10.1021/je60012a044 . [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]

Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [all data]

Van Hook, 1967
Van Hook, W. Alexander, Vapor Pressures of the Methylacetylenes, H3CCCH, H3CCCD, D3CCCH, and D3CCCD, J. Chem. Phys., 1967, 46, 5, 1907, https://doi.org/10.1063/1.1840952 . [all data]

Booth, Burchfield, et al., 1933
Booth, Harold Simmons; Burchfield, Paul E.; Bixby, Eva May; McKelvey, J.B., Fluorochloroethylenes, J. Am. Chem. Soc., 1933, 55, 6, 2231-2235, https://doi.org/10.1021/ja01333a005 . [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]

van Hook, 1967
van Hook, W.A., Vapor Pressures of the Methylacetylenes, H3CCCH, H3CCCD, D3CCCH, and D3CCCD, J. Chem. Phys., 1967, 46, 5, 1907-1918, https://doi.org/10.1063/1.1840952 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

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]

Parr, Jason, et al., 1979
Parr, A.C.; Jason, A.J.; Stockbauer, R.; McCulloh, K.E., Photoionization and threshold photoelectron-photoion coincidence study of propyne from onset to 20 eV, Int. J. Mass Spectrom. Ion Phys., 1979, 30, 319. [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]

Carlier, Dubois, et al., 1975
Carlier, P.; Dubois, J.E.; Masclet, P.; Mouvier, G., Spectres de photoelectrons des alcynes, J. Electron Spectrosc. Relat. Phenom., 1975, 7, 55. [all data]

Brogli, Heilbronner, et al., 1973
Brogli, F.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E., 230. Die photoelektronen-spektren methyl-substituierter Acetylene, Helv. Chim. Acta, 1973, 56, 2171. [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]

Person and Nicole, 1970
Person, J.C.; Nicole, P.P., Isotope effects in the photoionization yields and the absorption cross sections for acetylene, propyne, and propene, J. Chem. Phys., 1970, 53, 1767. [all data]

Frost, Herring, et al., 1970
Frost, D.C.; Herring, F.G.; McDowell, C.A.; Stenhouse, I.A., The ionization potentials of methyl cyanide and methyl acetylene by photoelectron spectroscopy and semi-rigorous LCAO SCF calculations, Chem. Phys. Lett., 1970, 4, 533. [all data]

Omura, Kaneko, et al., 1969
Omura, I.; Kaneko, T.; Yamada, Y.; Tanaka, K., Mass spectrometric studies of photoionization. IV. Acetylene and propyne, J. Phys. Soc. Japan, 1969, 27, 178. [all data]

Matthews and Warneck, 1969
Matthews, C.S.; Warneck, P., Heats of formation of CHO+ and C3H3+ by photoionization, J. Chem. Phys. 5, 1969, 1, 854. [all data]

Parr and Elder, 1968
Parr, A.C.; Elder, F.A., Photoionization of 1,3butadiene, 1,2-butadiene, allene, and propyne, J. Chem. Phys., 1968, 49, 2659. [all data]

Baker and Turner, 1968
Baker, C.; Turner, D.W., High resolution molecular photoelectron spectroscopy. III.Acetylenes and azaacetylenes, Proc. Roy. Soc. (London), 1968, A308, 19. [all data]

Gil'burd, Syrvatka, et al., 1967
Gil'burd, M.M.; Syrvatka, B.G.; Shevchuk, V.U.; Bel'ferman, A.L.; Moin, F.B., Mass spectrometric study of fluorine-containing compounds. I. Comparative study of methylacetylene and difluoromethylacetylene, High Energy Chem., 1967, 1, 359, In original 411. [all data]

Watanabe and Namioka, 1956
Watanabe, K.; Namioka, T., Ionization potential of propyne, J. Chem. Phys., 1956, 24, 915. [all data]

Bieri and Asbrink, 1980
Bieri, G.; Asbrink, L., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 20, 149. [all data]

Andreocci, Bitchev, et al., 1979
Andreocci, M.V.; Bitchev, P.; Carusi, P.; Furlani, A., Valence shell photoionization spectra of some substituted hydroxy-acetylenes. A tentative correlation with their cyclotrimerization reactions, J. Electron Spectrosc. Relat. Phenom., 1979, 16, 25. [all data]

SenSharma and Franklin, 1973
SenSharma, D.K.; Franklin, J.L., Heat of formation of free radicals by mass spectrometry, J. Am. Chem. Soc., 1973, 95, 6562. [all data]

Coats and Anderson, 1957
Coats, F.H.; Anderson, R.C., Thermodynamic data from electron-impact measurements on acetylene and substituted acetylenes, J. Am. Chem. Soc., 1957, 79, 1340. [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]

Gal, Decouzon, et al., 2001
Gal, J.F.; Decouzon, M.; Maria, P.C.; Gonzalez, A.I.; Mo, O.; Yanez, M.; El Chaouch, S.; Guillemin, J.C., Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes, J. Am. Chem. Soc., 2001, 123, 26, 6353-6359, https://doi.org/10.1021/ja004079j . [all data]

Robinson, Polak, et al., 1995
Robinson, M.S.; Polak, M.L.; Bierbaum, V.M.; DePuy, C.H.; Lineberger, W.C., Experimental Studies of Allene, Methylacetylene, and the Propargyl Radical: Bond Dissociation Energies, Gas-Phase Acidities, and Ion-Molecule Chemistry, J. Am. Chem. Soc., 1995, 117, 25, 6766, https://doi.org/10.1021/ja00130a017 . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References