1,3-Butadiyne
- Formula: C4H2
- Molecular weight: 50.0587
- 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 ion energetics data
Go To: Top, Mass spectrum (electron ionization), 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
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 |
Mass spectrum (electron ionization)
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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 87 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 |
---|---|---|---|---|---|
Capillary | CP Sil 5 CB | 20. | 431. | Do and Raulin, 1992 | 25. m/0.15 mm/2. μm, H2 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 445. | Kaiser and Siegl, 1994 | 60. m/0.32 mm/1. μm, -50. C @ 4. min, 6. K/min; Tend: 180. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 428. | 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 | 430. | 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 ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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]
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]
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]
Do and Raulin, 1992
Do, L.; Raulin, F.,
Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column,
J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R
. [all data]
Kaiser and Siegl, 1994
Kaiser, E.W.; Siegl, W.O.,
High resolution gas chromatographic determination of the atmospheric reactivity of engine-out hydrocarbon emissions from a spark-ignited engine,
J. Hi. Res. Chromatogr., 1994, 17, 4, 264-270, https://doi.org/10.1002/jhrc.1240170414
. [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
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance 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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