1,3-Butadiyne
- Formula: C4H2
- Molecular weight: 50.0587
- IUPAC Standard InChI: InChI=1S/C4H2/c1-3-4-2/h1-2H
- IUPAC Standard InChIKey: LLCSWKVOHICRDD-UHFFFAOYSA-N
- CAS Registry Number: 460-12-8
- 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: Butadiyne; Biacetylene; Biethynyl; Diacetylene; HC≡CC≡CH; buta-1,3-diyne
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry 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 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 | 464. | kJ/mol | Kin | Kiefer, Sidhu, et al., 1992 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 30.30 | 50. | Dorofeeva O.V., 1991 | Recommended values are in good agreement with other statistically calculated values [52FER/WER]. There is an appreciable difference with values calculated by [ Dessau L., 1988] because these authors used the estimated values of vibrational frequencies instead of experimental ones.; GT |
| 37.87 | 100. | ||
| 47.35 | 150. | ||
| 57.50 | 200. | ||
| 70.17 | 273.15 | ||
| 73.7 ± 1.0 | 298.15 | ||
| 73.92 | 300. | ||
| 84.43 | 400. | ||
| 91.51 | 500. | ||
| 96.86 | 600. | ||
| 101.26 | 700. | ||
| 105.05 | 800. | ||
| 108.38 | 900. | ||
| 111.33 | 1000. | ||
| 113.93 | 1100. | ||
| 116.24 | 1200. | ||
| 118.27 | 1300. | ||
| 120.06 | 1400. | ||
| 121.64 | 1500. | ||
| 123.04 | 1600. | ||
| 124.27 | 1700. | ||
| 125.37 | 1800. | ||
| 126.34 | 1900. | ||
| 127.20 | 2000. |
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: John E. Bartmess
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
C4H- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1507. ± 13. | kJ/mol | D-EA | Pino, Tulej, et al., 2002 | gas phase |
| ΔrH° | 1508. ± 12. | kJ/mol | Endo | Shi and Ervin, 2000 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1473. ± 14. | kJ/mol | H-TS | Pino, Tulej, et al., 2002 | gas phase |
| ΔrG° | 1474. ± 13. | kJ/mol | H-TS | Shi and Ervin, 2000 | gas phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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
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 C4H2+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 737.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 712.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.17 | PE | Bieri, Schmelzer, et al., 1980 | LLK |
| 10.17 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
| 10.1 ± 0.1 | EI | Reeher, Flesch, et al., 1976 | LLK |
| 10.17 | PE | Brogli, Heilbronner, et al., 1973 | LLK |
| 10.180 ± 0.003 | S | Smith, 1967 | RDSH |
| 10.17 ± 0.01 | PE | Baker and Turner, Commun. 1967 | RDSH |
| 10.30 | PE | Bieri and Asbrink, 1980 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H+ | 20.1 ± 0.5 | C2H | EI | Coats and Anderson, 1957 | RDSH |
| C4H+ | 12.1 ± 0.3 | H | EI | Coats and Anderson, 1957 | RDSH |
De-protonation reactions
C4H- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1507. ± 13. | kJ/mol | D-EA | Pino, Tulej, et al., 2002 | gas phase; B |
| ΔrH° | 1508. ± 12. | kJ/mol | Endo | Shi and Ervin, 2000 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1473. ± 14. | kJ/mol | H-TS | Pino, Tulej, et al., 2002 | gas phase; B |
| ΔrG° | 1474. ± 13. | kJ/mol | H-TS | Shi and Ervin, 2000 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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.
Kiefer, Sidhu, et al., 1992
Kiefer, J.H.; Sidhu, S.S.; Kern, R.D.; Xie, K.; Chen, H.; Harding, L.B.,
The homogeneous pyrolysis of acetylene II: the high temperature radical chain mechanism,
Combust. Sci. Technol., 1992, 82, 101-130. [all data]
Dorofeeva O.V., 1991
Dorofeeva O.V.,
Thermodynamic properties of linear carbon chain molecules with conjugated triple bonds. Part I. Polyacetylenes, H(CC)nH (n=2-6), cyanopolyacetylenes, H(CC)nCN (n=1-5), and dicyanopolyacetylenes, NC(CC)nCN (n=1-4),
Thermochim. Acta, 1991, 178, 273-286. [all data]
Dessau L., 1988
Dessau L.,
Vibrations and thermodynamic functions of long-chain acetylenes,
Z. Phys. Chem. (Leipzig), 1988, 269, 187-190. [all data]
Pino, Tulej, et al., 2002
Pino, T.; Tulej, M.; Guthe, F.; Pachkov, M.; Maier, J.P.,
Photodetachment spectroscopy of the C2nH- (n=2-4) anions in the vicinity of their electron detachment threshold,
J. Chem. Phys., 2002, 116, 14, 6126-6131, https://doi.org/10.1063/1.1451248
. [all data]
Shi and Ervin, 2000
Shi, Y.; Ervin, K.M.,
Gas-phase acidity and C-H bond energy of diacetylene,
Chem. Phys. Lett., 2000, 318, 1-3, 149-154, https://doi.org/10.1016/S0009-2614(00)00023-3
. [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, Schmelzer, et al., 1980
Bieri, G.; Schmelzer, A.; Asbrink, L.; Jonsson, M.,
Fluorine and the fluoroderivatives of acetylene and diacetylene studied by 30.4 nm He(II) photoelectron spectroscopy,
Chem. Phys., 1980, 49, 213. [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]
Reeher, Flesch, et al., 1976
Reeher, J.R.; Flesch, G.D.; Svec, H.J.,
The mass spectra and ionization potentials of the neutral fragments produced during the electron bombardment of aromatic compounds,
Org. Mass Spectrom., 1976, 11, 154. [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]
Smith, 1967
Smith, W.L.,
The absorption spectrum of diacetylene in the vacuum ultraviolet,
Proc. Roy. Soc. (London), 1967, A300, 519. [all data]
Baker and Turner, Commun. 1967
Baker, C.; Turner, D.W.,
Photoelectron spectra of acetylene, diacetylene, and their deutero-derivatives,
Chem., Commun. 1967, 797. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas 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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