1-Buten-3-yne
- Formula: C4H4
- Molecular weight: 52.0746
- IUPAC Standard InChI: InChI=1S/C4H4/c1-3-4-2/h1,4H,2H2
- IUPAC Standard InChIKey: WFYPICNXBKQZGB-UHFFFAOYSA-N
- CAS Registry Number: 689-97-4
- 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-1-en-3-yne; Butenyne; Ethene, ethynyl-; Monovinylacetylene; Vinylacetylene; 1-Butene-3-yne; 1-Butyn-3-ene; 3-Buten-1-yne; Buten-3-yne; Ethynylethene; 1-Butenyne; Vinylethyne
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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 | 295. | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 73.18 | 298.15 | Stamm R.F., 1949 | Estimations by difference method and Benson group additivity approach [ Dorofeeva O.V., 1997] show that statistically calculated value of S(298 K) can be overestimated by 5-7 J/mol*K and uncertainties of Cp(T) values can be equal to 4-7 J/mol*K.; GT |
| 73.51 | 300. | ||
| 88.95 | 400. | ||
| 101.46 | 500. | ||
| 111.59 | 600. | ||
| 120.00 | 700. | ||
| 127.19 | 800. | ||
| 133.34 | 900. | ||
| 138.74 | 1000. | ||
| 156.98 | 1100. |
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 by: 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
2 =
By formula: 2C2H2 = C4H4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 233. | kJ/mol | Cm | Reppe, Schlichting, et al., 1948 | liquid phase |
| ΔrH° | 208. | kJ/mol | Cm | Reppe, Schlichting, et al., 1948 | gas phase |
3 +
=
By formula: 3H2 + C4H4 = C4H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -422. ± 2. | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
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:
L - Sharon G. Lias
Data compiled as indicated in comments:
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 C4H4+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.58 ± 0.02 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.58 ± 0.02 | EI | Rosenstock, McCulloh, et al., 1977 | LLK |
| 9.58 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
| 9.58 ± 0.02 | PE | Brogli, Heilbronner, et al., 1975 | LLK |
| 9.63 | PE | Bruckmann and Klessinger, 1973 | LLK |
| 9.9 | EI | Li and McGee, 1969 | RDSH |
| 9.9 | EI | Hedaya, Miller, et al., 1969 | RDSH |
| 9.87 | EI | Varsel, Morrell, et al., 1960 | RDSH |
| 9.9 | EI | Polyakova, Zimina, et al., 1960 | RDSH |
| 9.9 | EI | Polyakova, Zimina, et al., 1959 | RDSH |
| 9.64 ± 0.03 | PE | Van Hoorn, 1975 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H+ | 18.71 | ? | EI | Field, Franklin, et al., 1957 | RDSH |
| C4H+ | 12.13 | H2+H | EI | Field, Franklin, et al., 1957 | RDSH |
| C4H2+ | 12.84 | H2 | EI | Field, Franklin, et al., 1957 | RDSH |
| C4H3+ | 12.59 | H | EI | Field, Franklin, et al., 1957 | RDSH |
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. | 373. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 49. | 373. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 67. | 374. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 86. | 374. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH-100 | 407.15 | 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) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 404. | 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 | 410. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Stamm R.F., 1949
Stamm R.F.,
Fundamental vibrational frequencies and thermodynamic functions for vinylacetylene, revised thermodynamic functions for hydrogen cyanide, and thermodynamics of two reactions involved in the synthesis of acrylonitrile,
J. Chem. Phys., 1949, 17, 104-105. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Reppe, Schlichting, et al., 1948
Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T.,
Cyclisierende Polymerisation von Acetylen I Uber Cyclooctatetraen,
Justus Liebigs Ann. Chem., 1948, 1-93. [all data]
Rosenstock, McCulloh, et al., 1977
Rosenstock, H.M.; McCulloh, K.E.; Lossing, F.P.,
On the mechanisms of C6H6 ionization fragmentation,
Int. J. Mass Spectrom. Ion Phys., 1977, 25, 327. [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]
Brogli, Heilbronner, et al., 1975
Brogli, F.; Heilbronner, E.; Wirz, J.; Kloster-Jensen, E.; Bergman, R.G.; Vollhardt, K.P.C.; Ashe, A.J., III,
The consequences of σ and π conjugative interactions in mono-, di- and triacetylenes. A photoelectron spectroscopic investigation,
Helv. Chim. Acta, 1975, 58, 2620. [all data]
Bruckmann and Klessinger, 1973
Bruckmann, P.; Klessinger, M.,
Photoelektronenspektren organischer verbindungen. III. Photoelektronenspektren acetylensubstituierter kleiner ringe,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 341. [all data]
Li and McGee, 1969
Li, P.H.; McGee, H.A., Jr.,
Mass spectrum and ionization potential of condensed cyclobutadiene,
Chem. Commun., 1969, 592. [all data]
Hedaya, Miller, et al., 1969
Hedaya, E.; Miller, R.D.; McNeil, D.W.; D'Angelo, P.F.; Schissel, P.,
Flash vacuum pyrolysis. V. Cyclobutadiene,
J. Am. Chem. Soc., 1969, 91, 1875. [all data]
Varsel, Morrell, et al., 1960
Varsel, C.J.; Morrell, F.A.; Resnik, F.E.; Powell, W.A.,
Qualitative and quantitative analysis of organic compounds. Use of low-voltage mass spectrometry,
Anal. Chem., 1960, 32, 182. [all data]
Polyakova, Zimina, et al., 1960
Polyakova, A.A.; Zimina, K.I.; Petrov, A.A.; Khmel'nitskii, R.A.,
Mass spectra of vinylalkylacetylenes,
Zh. Obshch. Khim., 1960, 30, 912, In original 927. [all data]
Polyakova, Zimina, et al., 1959
Polyakova, A.A.; Zimina, K.I.; Petrov, A.A.; Klmel'nitskii, R.A.,
Mass Spectra and the structure of vinylacetylenes,
Dokl. Phys. Chem., 1959, 127, 597, In original 386. [all data]
Van Hoorn, 1975
Van Hoorn, M.D.,
He(I) ionisation potentials and MO calculations of butenyne and the monomethyl-substituted butenynes,
J. Electron Spectrosc. Relat. Phenom., 1975, 6, 65. [all data]
Field, Franklin, et al., 1957
Field, F.H.; Franklin, J.L.; Lampe, F.W.,
Reactions of gaseous ions. II. Acetylene,
J. Am. Chem. Soc., 1957, 79, 2665. [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]
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]
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]
Notes
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- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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