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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Gas phase ion energetics data
Go To: Top, 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 |
References
Go To: Top, 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.
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 ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy 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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