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
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Isotopologues:
- Butadiyne-d2
Other names: Butadiyne; Biacetylene; Biethynyl; Diacetylene; HC≡CC≡CH; buta-1,3-diyne
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Gas phase ion energetics data

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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^- + = 1,3-Butadiyne

By formula: C₄H^- + H⁺ = C₄H₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1507. ± 13.	kJ/mol	D-EA	Pino, Tulej, et al., 2002	gas phase; B
Δ_rH°	1508. ± 12.	kJ/mol	Endo	Shi and Ervin, 2000	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1473. ± 14.	kJ/mol	H-TS	Pino, Tulej, et al., 2002	gas phase; B
Δ_rG°	1474. ± 13.	kJ/mol	H-TS	Shi and Ervin, 2000	gas phase; B

Gas Chromatography

Go To: Top, Gas phase ion energetics data, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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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

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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; T_end: 180. C

Normal alkane RI, non-polar column, temperature ramp

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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; T_start: 50. C; T_end: 250. C

References

Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes

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, Gas Chromatography, References

Symbols used in this document:

AE Appearance energy

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions