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
View 3d structure (requires JavaScript / HTML 5) - Isotopologues:
- Other names: Methylacetylene; 1-Propyne; Allylene; Propine; CH3C≡CH; Acetylene, methyl-
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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 |
---|---|---|---|---|---|
ΔfH°gas | 185.4 ± 0.88 | kJ/mol | Ccb | Wagman, Kilpatrick, et al., 1945 | Unpublished work of E. J. Prosen; ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.37 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Recommended values are in good agreement with other statistically calculated values [ Wagman D.D., 1945, Daykin P.N., 1962].; GT |
36.69 | 100. | ||
42.44 | 150. | ||
48.56 | 200. | ||
57.65 | 273.15 | ||
60.73 | 298.15 | ||
60.95 | 300. | ||
72.54 | 400. | ||
82.61 | 500. | ||
91.23 | 600. | ||
98.69 | 700. | ||
105.22 | 800. | ||
110.96 | 900. | ||
116.01 | 1000. | ||
120.43 | 1100. | ||
124.31 | 1200. | ||
127.70 | 1300. | ||
130.67 | 1400. | ||
133.28 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
57.57 | 272.28 | Kistiakowsky G.B., 1940 | Other experimental values of heat capacity [ Kistiakowsky G.B., 1940, 2] were measured with large uncertainties.; GT |
61.00 | 299.59 | ||
65.10 | 332.83 | ||
69.12 | 369.21 |
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
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) | 748. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 723.0 | kJ/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° | 1591. ± 8.8 | kJ/mol | G+TS | Gal, Decouzon, et al., 2001 | gas phase; B |
ΔrH° | 1597. ± 9.6 | kJ/mol | D-EA | Robinson, Polak, et al., 1995 | gas phase; B |
ΔrH° | 1595. ± 8.8 | kJ/mol | G+TS | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B |
ΔrH° | 1594. ± 8.8 | kJ/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° | 1559. ± 8.4 | kJ/mol | IMRE | Gal, Decouzon, et al., 2001 | gas phase; B |
ΔrG° | 1562. ± 8.4 | kJ/mol | IMRE | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B |
ΔrG° | 1562. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Ion clustering 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: Co+ + C3H4 = (Co+ • C3H4)
Enthalpy of reaction
ΔrH° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
79.1 (+8.8,-0.) | CID | Haynes and Armentrout, 1994 | gas phase; ΔrH>=, guided ion beam CID |
By formula: Li+ + C3H4 = (Li+ • C3H4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 119. | kJ/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated |
IR Spectrum
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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: Coblentz Society, Inc.
Gas Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | Copyright (C) 1987 by the Coblentz Society Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | DOW CHEMICAL COMPANY |
Source reference | COBLENTZ NO. 8880 |
Date | 1964 |
Name(s) | 1-propyne |
State | GAS (50 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg) |
Instrument | DOW KBr FOREPRISM-GRATING |
Instrument parameters | GRATING CHANGED AT 5.0, 7.5, 15.0 MICRON |
Path length | 5 CM SPECTRAL CONTAMINATION DUE TO ACETYLENE AT 732 CM-1 ROTATIONAL FEATURES BETWEEN 3090-2971 CM-1 ARE DELETED |
Resolution | 2 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY |
Vibrational and/or electronic energy levels
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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: Takehiko Shimanouchi
Symmetry: C3ν Symmetry Number σ = 3
Sym. | No | Approximate | Selected Freq. | Infrared | Raman | Comments | ||||
---|---|---|---|---|---|---|---|---|---|---|
Species | type of mode | Value | Rating | Value | Phase | Value | Phase | |||
a1 | 1 | CH str | 3334 | C | 3334 | gas | 3305 M | liq. | ||
a1 | 2 | CH3 s-str | 2918 | E | 2941 M | gas | 2941 VS p | liq. | FR(ν2+2ν7) | |
a1 | 2 | CH3 s-str | 2918 | E | 2881 M | gas | 2941 VS p | liq. | FR(ν2+2ν7) | |
a1 | 3 | C≡C str | 2142 | A | 2142.2 M | gas | 2142 VS p | liq. | ||
a1 | 4 | CH3 s-deform | 1382 | D | 1382 S dp | liq. | ||||
a1 | 5 | C-C str | 931 | C | 930.7 W | gas | 930 S p | gas | ||
e | 6 | CH3 d-str | 3008 | A | 3008.3 M | gas | 2971 M | liq. | ||
e | 7 | CH3 d-deform | 1452 | B | 1452 M | gas | 1448 M | liq. | ||
e | 8 | CH3 rock | 1053 | A | 1052.5 W | gas | 1035 VW | liq. | ||
e | 9 | CH bend | 633 | C | 633 S | gas | 643 S dp | liq. | ||
e | 10 | CCC bend | 328 | C | 328 W | gas | 336 VS dp | liq. | ||
Source: Shimanouchi, 1972
Notes
VS | Very strong |
S | Strong |
M | Medium |
W | Weak |
VW | Very weak |
p | Polarized |
dp | Depolarized |
FR | Fermi resonance with an overtone or a combination tone indicated in the parentheses. |
A | 0~1 cm-1 uncertainty |
B | 1~3 cm-1 uncertainty |
C | 3~6 cm-1 uncertainty |
D | 6~15 cm-1 uncertainty |
E | 15~30 cm-1 uncertainty |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Vibrational and/or electronic energy levels, 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]
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]
Haynes and Armentrout, 1994
Haynes, C.L.; Armentrout, P.B.,
Thermochemistry and Structures of CoC3H6+: Metallacyclic and Metal-Alkene Isomers,
Organomettalics, 1994, 13, 9, 3480, https://doi.org/10.1021/om00021a022
. [all data]
Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L.,
Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050
. [all data]
Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P.,
Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013
. [all data]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Vibrational and/or electronic energy levels, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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