Propyne
- Formula: C3H4
- Molecular weight: 40.0639
- IUPAC Standard InChIKey: MWWATHDPGQKSAR-UHFFFAOYSA-N
- CAS Registry Number: 74-99-7
- 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. - Isotopologues:
- Other names: Methylacetylene; 1-Propyne; Allylene; Propine; CH3C≡CH; Acetylene, methyl-
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Phase change data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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 |
---|---|---|---|---|---|
Tboil | 250.0 ± 0.5 | K | AVG | N/A | Average of 18 out of 19 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 170.2 ± 0.6 | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 168.5 | K | N/A | Maass and Wright, 1921 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 402.4 ± 0.2 | K | N/A | Tsonopoulos and Ambrose, 1996 | |
Tc | 402.38 | K | N/A | Vohra, Kang, et al., 1962 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tc | 401.1 | K | N/A | Maass and Wright, 1921 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 55.6 ± 0.2 | atm | N/A | Tsonopoulos and Ambrose, 1996 | |
Pc | 55.5400 | atm | N/A | Vohra, Kang, et al., 1962 | Uncertainty assigned by TRC = 0.0499 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.1635 | l/mol | N/A | Tsonopoulos and Ambrose, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 6.12 ± 0.02 | mol/l | N/A | Tsonopoulos and Ambrose, 1996 | |
ρc | 6.113 | mol/l | N/A | Vohra, Kang, et al., 1962 | Uncertainty assigned by TRC = 0.01 mol/l; TRC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.50 | 242. | A | Stephenson and Malanowski, 1987 | Based on data from 183. to 257. K.; AC |
4.97 | 272. | A | Stephenson and Malanowski, 1987 | Based on data from 257. to 402. K.; AC |
5.07 | 318. | A | Stephenson and Malanowski, 1987 | Based on data from 303. to 361. K.; AC |
5.23 | 374. | A | Stephenson and Malanowski, 1987 | Based on data from 359. to 402. K.; AC |
5.54 | 264. | A | Stephenson and Malanowski, 1987 | Based on data from 249. to 306. K.; AC |
5.28 | 275. | N/A | Reid, 1972 | AC |
5.71 | 240. | N/A | Van Hook, 1967 | Based on data from 162. to 255. K.; AC |
5.16 | 338. | N/A | Vohra, Kang, et al., 1962 | Based on data from 323. to 400. K.; AC |
5.59 | 235. | N/A | Booth, Burchfield, et al., 1933 | Based on data from 194. to 250. K. See also Boublik, Fried, et al., 1984.; AC |
5.11 | 230. | N/A | Maass and Wright, 1921 | Based on data from 200. to 260. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
161.5 to 254.27 | 4.94648 | 1226.123 | -1.926 | van Hook, 1967 | Coefficents calculated by NIST from author's data. |
249.9 to 398. | 4.02498 | 818.384 | -46.457 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change data, Mass spectrum (electron ionization), 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 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 179. | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 172.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.37 | PE | Kimura, Katsumata, et al., 1981 | LLK |
10.37 ± 0.01 | PI | Parr, Jason, et al., 1979 | LLK |
10.38 ± 0.01 | TE | Parr, Jason, et al., 1979 | LLK |
10.37 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
10.364 ± 0.005 | PE | Carlier, Dubois, et al., 1975 | LLK |
10.37 | PE | Brogli, Heilbronner, et al., 1973 | LLK |
10.36 | EI | Lossing, 1972 | LLK |
10.365 ± 0.015 | PI | Person and Nicole, 1970 | RDSH |
10.37 | PE | Frost, Herring, et al., 1970 | RDSH |
10.349 ± 0.015 | PI | Omura, Kaneko, et al., 1969 | RDSH |
10.36 ± 0.02 | PI | Matthews and Warneck, 1969 | RDSH |
10.38 ± 0.02 | PI | Parr and Elder, 1968 | RDSH |
10.37 ± 0.01 | PE | Baker and Turner, 1968 | RDSH |
10.5 ± 0.1 | EI | Gil'burd, Syrvatka, et al., 1967 | RDSH |
10.36 | S | Watanabe and Namioka, 1956 | RDSH |
10.36 ± 0.01 | PI | Watanabe and Namioka, 1956 | RDSH |
10.37 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.54 | PE | Bieri and Asbrink, 1980 | Vertical value; LLK |
10.36 | PE | Andreocci, Bitchev, et al., 1979 | Vertical value; LLK |
Appearance energy determinations
De-protonation reactions
C3H3- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 380.3 ± 2.1 | kcal/mol | G+TS | Gal, Decouzon, et al., 2001 | gas phase; B |
ΔrH° | 381.8 ± 2.3 | kcal/mol | D-EA | Robinson, Polak, et al., 1995 | gas phase; B |
ΔrH° | 381.1 ± 2.1 | kcal/mol | G+TS | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B |
ΔrH° | 381.0 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 372.6 ± 2.0 | kcal/mol | IMRE | Gal, Decouzon, et al., 2001 | gas phase; B |
ΔrG° | 373.4 ± 2.0 | kcal/mol | IMRE | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B |
ΔrG° | 373.3 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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 | 18849 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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