2-Butyne
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChIKey: XNMQEEKYCVKGBD-UHFFFAOYSA-N
- CAS Registry Number: 503-17-3
- 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. - Other names: But-2-yne; Dimethylacetylene; CH3C≡CCH3; Crotonylene; UN 1144
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 300. ± 1. | K | AVG | N/A | Average of 23 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 240.82 | K | N/A | Pomerantz, Fookson, et al., 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 240.9 | K | N/A | Boord, Greenlee, et al., 1946 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 240.63 | K | N/A | Boord, Greenlee, et al., 1946 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 240.83 | K | N/A | Henne and Greenlee, 1945 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 240.5 | K | N/A | Heisig and Davis, 1935 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 240.8 | K | N/A | Yost, Osborne, et al., 1941 | Uncertainty assigned by TRC = 0.15 K; TRC |
Ttriple | 240.93 | K | N/A | Yost, Osborne, et al., 1941 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 6.38 | kcal/mol | N/A | Reid, 1972 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.4400 | 291.0 | N/A | Yost, Osborne, et al., 1941, 2 | P = 71.46 kPa; DH |
6.4400 | 291.00 | N/A | Osborne, Garner, et al., 1940 | DH |
6.9 | 255. | A | Stephenson and Malanowski, 1987 | Based on data from 240. to 308. K.; AC |
6.44 ± 0.06 | 291.00 | C | Yost, Osborne, et al., 1941, 3 | ALS |
6.43 ± 0.02 | 291. | C | Yost, Osborne, et al., 1941, 2 | AC |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
22.13 | 291.0 | Yost, Osborne, et al., 1941, 2 | P; DH |
22.13 | 291.00 | Osborne, Garner, et al., 1940 | DH |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.94 | 220. | A | Stull, 1947 | Based on data from 200. to 239. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.2072 | 240.92 | Yost, Osborne, et al., 1941, 2 | DH |
2.2067 | 240.93 | Osborne, Garner, et al., 1940 | DH |
2.21 | 240.9 | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.1654 | 240.92 | Yost, Osborne, et al., 1941, 2 | DH |
9.161 | 240.93 | Osborne, Garner, et al., 1940 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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 C4H6+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.58 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 185.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 178.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.59 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.562 ± 0.005 | PE | Carlier, Dubois, et al., 1975 | LLK |
9.61 | PE | Ensslin, Bock, et al., 1974 | LLK |
9.59 | PE | Brogli, Heilbronner, et al., 1973 | LLK |
9.56 | EI | Lossing, 1972 | LLK |
9.79 | PE | Bieri and Asbrink, 1980 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 17.6 ± 0.5 | ? | EI | Coats and Anderson, 1957 | RDSH |
C2H3+ | 14.7 ± 0.2 | ? | EI | Coats and Anderson, 1957 | RDSH |
C3H3+ | 11.04 | CH3 | EI | Lossing, 1972 | LLK |
C4H2+ | 16.7 ± 0.3 | ? | EI | Coats and Anderson, 1957 | RDSH |
C4H3+ | 15.1 ± 0.2 | H2+H | EI | Coats and Anderson, 1957 | RDSH |
C4H4+ | 14.0 ± 0.1 | H2 | EI | Coats and Anderson, 1957 | RDSH |
C4H5+ | 12.1 ± 0.1 | H | EI | Coats and Anderson, 1957 | RDSH |
De-protonation reactions
C4H5- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 389.2 ± 2.1 | kcal/mol | G+TS | Gal, Decouzon, et al., 2001 | gas phase; Acid: MeC≡CMe; B |
ΔrH° | 389.0 ± 3.3 | kcal/mol | G+TS | N/A | gas phase; Measured vs pyridine; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 381.7 ± 2.0 | kcal/mol | IMRE | Gal, Decouzon, et al., 2001 | gas phase; Acid: MeC≡CMe; B |
ΔrG° | 381.5 ± 3.2 | kcal/mol | IMRE | N/A | gas phase; Measured vs pyridine; B |
Gas Chromatography
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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Squalane | 27. | 463. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 463. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 463. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 462. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 26. | 473. | Zulaïca and Guiochon, 1966 | Column length: 10. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH-100 | 488. | Haagen-Smit Laboratory, 1997 | He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min) |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH | 478. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 485. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
Capillary | OV-101 | 466. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP-Sil5 CB MS | 482. | Tirillini, Verdelli, et al., 2000 | 50. m/0.32 mm/0.4 μm; Program: 0C (3min) => 3C/min => 50C => 5C/min => 220C (30min) |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pomerantz, Fookson, et al., 1954
Pomerantz, P.; Fookson, A.; Mears, T.W.; Rothberg, S.; Howard, F.L.,
Synthesis and Physical Properties of Several Acetylenic Hydrocarbons,
J. Res. Natl. Bur. Stand. (U. S.), 1954, 52, 51. [all data]
Boord, Greenlee, et al., 1946
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.,
The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Weight, Am. Pet. Inst. Res. Proj. 45, Eighth Annu. Rep., Ohio State Univ., June 30, 1946. [all data]
Henne and Greenlee, 1945
Henne, A.L.; Greenlee, K.W.,
Preparation and Physical Constants of Acetylenic Compounds,
J. Am. Chem. Soc., 1945, 67, 484-5. [all data]
Heisig and Davis, 1935
Heisig, G.B.; Davis, H.M.,
Physical Constants of Dimethylacetylene,
J. Am. Chem. Soc., 1935, 57, 339-40. [all data]
Yost, Osborne, et al., 1941
Yost, D.M.; Osborne, D.W.; Garner, C.S.,
The Heat Capacity, Entropy, and Heats of Transition, Fusion, and Vaporization of Dimethylacetylene. Free Rotation in the Dimethylacetylene Molecule,
J. Am. Chem. Soc., 1941, 63, 3492. [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]
Yost, Osborne, et al., 1941, 2
Yost, D.M.; Osborne, D.W.; Garner, C.S.,
The heat capacity, entropy, and heats of transition, fusion, and vaporization of dimethylacetylene. Free rotation in the dimethylacetylene molecule,
J. Am. Chem. Soc., 1941, 63, 3492-3496. [all data]
Osborne, Garner, et al., 1940
Osborne, D.W.; Garner, C.S.; Yost, D.M.,
The entropy of dimethylacetylene from low temperature calorimetric measurements. Free rotation in the dimethylacetylene molecule,
J. Chem. Phys., 1940, 8, 131. [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]
Yost, Osborne, et al., 1941, 3
Yost, D.M.; Osborne, D.W.; Garner, C.S.,
The heat capacity, entropy, and heats of transition, fusion, and vaporization of dimethylacetylene. Free rotation in the dimethylacetylene molecule,
J. Am. Chem. Soc., 1941, 63, 3492-34. [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]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
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]
Ensslin, Bock, et al., 1974
Ensslin, W.; Bock, H.; Becker, G.,
Photoelectron spectra and molecular properties. XXX. π interactions in H3Si- H3C-substituted acetylenes,
J. Am. Chem. Soc., 1974, 96, 2757. [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]
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]
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]
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]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
Zulaïca and Guiochon, 1966
Zulaïca, J.; Guiochon, G.,
Analyse des hauts polymères par chromatographie en phase gazeuse de leurs produits de pyrolyse. II. Application à quelques hydrocarbures macromoléculaires purs,
Bull. Soc. Chim. Fr., 1966, 4, 1351-1363. [all data]
Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory,
Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]
White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Bramston-Cook, 2013
Bramston-Cook, R.,
Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Tirillini, Verdelli, et al., 2000
Tirillini, B.; Verdelli, G.; Paolocci, F.; Ciccioli, P.; Frattoni, M.,
The volatile organic compounds from the mycelium of Tuber borchii Vitt.,
Phytochemistry, 2000, 55, 8, 983-985, https://doi.org/10.1016/S0031-9422(00)00308-3
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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