2-Butyne
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChI: InChI=1S/C4H6/c1-3-4-2/h1-2H3
- 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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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 | 145.1 ± 1.0 | kJ/mol | Cm | Prosen, Maron, et al., 1951 | ALS |
| ΔfH°gas | 148.0 ± 1.5 | kJ/mol | Ccb | Wagman, Kilpatrick, et al., 1945 | Unpublished work of E. J. Prosen; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°gas | -2576.7 ± 0.96 | kJ/mol | Cm | Prosen, Maron, et al., 1951 | Corresponding ΔfHºgas = 145.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 39.18 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Selected values are in close agreement with other statistically calculated values [ Wagman D.D., 1945].; GT |
| 48.43 | 100. | ||
| 56.69 | 150. | ||
| 63.57 | 200. | ||
| 74.10 | 273.15 | ||
| 78.02 | 298.15 | ||
| 78.32 | 300. | ||
| 94.73 | 400. | ||
| 110.38 | 500. | ||
| 124.30 | 600. | ||
| 136.49 | 700. | ||
| 147.14 | 800. | ||
| 156.45 | 900. | ||
| 164.55 | 1000. | ||
| 171.59 | 1100. | ||
| 177.71 | 1200. | ||
| 183.0 | 1300. | ||
| 187.6 | 1400. | ||
| 191.7 | 1500. |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 84.56 | 336.07 | Kistiakowsky G.B., 1940 | GT |
| 89.66 | 369.46 |
Reaction 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C4H5- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1628. ± 8.8 | kJ/mol | G+TS | Gal, Decouzon, et al., 2001 | gas phase; Acid: MeC≡CMe; B |
| ΔrH° | 1628. ± 14. | kJ/mol | G+TS | N/A | gas phase; Measured vs pyridine; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1597. ± 8.4 | kJ/mol | IMRE | Gal, Decouzon, et al., 2001 | gas phase; Acid: MeC≡CMe; B |
| ΔrG° | 1596. ± 13. | kJ/mol | IMRE | N/A | gas phase; Measured vs pyridine; B |
2 +
=
By formula: 2H2 + C4H6 = C4H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -272.4 ± 1.3 | kJ/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -274.4 ± 0.54 kJ/mol; At 355 K; ALS |
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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| Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center |
| State | gas |
| Instrument | HP-GC/MS/IRD |
Gas Chromatography
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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: 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, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Prosen, Maron, et al., 1951
Prosen, E.J.; Maron, F.W.; Rossini, F.D.,
Heats of combustion, formation, and insomerization of ten C4 hydrocarbons,
J. Res. NBS, 1951, 46, 106-112. [all data]
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]
Kistiakowsky G.B., 1940
Kistiakowsky G.B.,
Gaseous heat capacities. III,
J. Chem. Phys., 1940, 8, 618-622. [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]
Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A.,
Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes,
J. Am. Chem. Soc., 1939, 61, 1868-1876. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas ΔcH°gas Enthalpy of combustion of gas at standard conditions 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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