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:
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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 thermochemistry data

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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
Δ_fH°_gas	464.	kJ/mol	Kin	Kiefer, Sidhu, et al., 1992	ALS

Constant pressure heat capacity of gas

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

Henry's Law data

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Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

k°_H (mol/(kg*bar))	d(ln(k_H))/d(1/T) (K)	Method	Reference	Comment
0.19		Q	N/A	missing citation give several references for the Henry's law constants but don't assign them to specific species.

Gas Chromatography

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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

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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]

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

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
d(ln(k_H))/d(1/T)	Temperature dependence parameter for Henry's Law constant
k°_H	Henry's Law constant at 298.15K
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
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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