Selected ATcT [1, 2] enthalpy of formation based on version 1.176 of the Thermochemical Network [3]

This version of ATcT results[3] was generated by additional expansion of version 1.172 to include species related to Criegee intermediates that are involved in several ongoing studies[4].

1,3-Butadiyne

Formula: HCCCCH (g)

CAS RN: 460-12-8

ATcT ID: 460-12-8*0

SMILES: C#CC#C

InChI: InChI=1S/C4H2/c1-3-4-2/h1-2H

InChIKey: LLCSWKVOHICRDD-UHFFFAOYSA-N

Hills Formula: C4H2

2D Image:

Aliases: HCCCCH; 1,3-Butadiyne; Butadiyne; Diacetylene; Biacetylene; Biethynyl

Relative Molecular Mass: 50.0587 ± 0.0032

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
458.35	460.08	± 0.48	kJ/mol

3D Image of HCCCCH (g)

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Top contributors to the provenance of Δ_fH° of HCCCCH (g)

The 20 contributors listed below account only for 45.6% of the provenance of Δ_fH° of HCCCCH (g).
A total of 339 contributors would be needed to account for 90% of the provenance.

Please note: The list is limited to 20 most important contributors or, if less, a number sufficient to account for 90% of the provenance. The Reference acts as a further link to the relevant references and notes for the measurement. The Measured Quantity is normaly given in the original units; in cases where we have reinterpreted the original measurement, the listed value may differ from that given by the authors. The quoted uncertainty is the a priori uncertainty used as input when constructing the initial Thermochemical Network, and corresponds either to the value proposed by the original authors or to our estimate; if an additional multiplier is given in parentheses immediately after the prior uncertainty, it corresponds to the factor by which the prior uncertainty needed to be multiplied during the ATcT analysis in order to make that particular measurement consistent with the prevailing knowledge contained in the Thermochemical Network.

Contribution (%)	TN ID	Reaction	Measured Quantity	Reference
10.5	6830.10	2 HCCH (g) → HCCCCH (g) + H2 (g)	Δ_rH°(0 K) = 0.03 ± 0.3 kcal/mol	Simmonett 2009
6.3	6838.6	3 HCCH (g) → HCCCCCCH (g) + 2 H2 (g)	Δ_rH°(0 K) = -2.60 ± 2.00 kJ/mol	Klippenstein 2017
5.1	6829.1	4 CH4 (g) → HCCCCH (g) + 7 H2 (g)	Δ_rH°(0 K) = 724.15 ± 2.00 kJ/mol	Klippenstein 2017
3.2	6915.9	C6H4 (g, singlet) → HCCCCH (g) + HCCH (g)	Δ_rH°(0 K) = 52.4 ± 0.5 kcal/mol	Zhang 2007
2.6	9272.1	4 CH4 (g) → CCCCH (g) + 15/2 H2 (g)	Δ_rH°(0 K) = 1068.39 ± 2.00 kJ/mol	Klippenstein 2017
2.4	6837.6	HCCCCCCH (g) + HCCH (g) → 2 HCCCCH (g)	Δ_rH°(0 K) = 5.15 ± 2.00 kJ/mol	Klippenstein 2017
1.9	7984.9	HCCCN (g) + HCCH (g) → HCCCCH (g) + HCN (g)	Δ_rH°(0 K) = -13.68 ± 2.0 kJ/mol	Klippenstein 2017
1.6	9038.1	5 CH4 (g) → HCCCCCH3 (g) + 8 H2 (g)	Δ_rH°(0 K) = 750.67 ± 2.00 kJ/mol	Klippenstein 2017
1.2	6833.6	HCCCCCCH (g) → 6 C (g) + 2 H (g)	Δ_rH°(0 K) = 960.4 ± 1.2 kcal/mol	Bakowies 2020
1.1	6831.8	HCCCCH (g) + 2 CH4 (g) → CH3CH3 (g) + 2 HCCH (g)	Δ_rH°(0 K) = 15.07 ± 0.9 kcal/mol	Ruscic W1RO
1.1	6832.8	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 11.48 ± 0.9 kcal/mol	Ruscic W1RO
1.0	2375.1	2 H2 (g) + C (graphite) → CH4 (g)	Δ_rG°(1165 K) = 37.521 ± 0.068 kJ/mol	Smith 1946, note COf, 3rd Law
1.0	6838.5	3 HCCH (g) → HCCCCCCH (g) + 2 H2 (g)	Δ_rH°(0 K) = -1.13 ± 1.2 kcal/mol	Ruscic W1RO
0.9	9086.1	5 CH4 (g) → HCCCCCH2 (g) + 17/2 H2 (g)	Δ_rH°(0 K) = 901.27 ± 2.00 kJ/mol	Klippenstein 2017
0.9	6831.4	HCCCCH (g) + 2 CH4 (g) → CH3CH3 (g) + 2 HCCH (g)	Δ_rH°(0 K) = 15.68 ± 1.0 kcal/mol	Ruscic G4
0.9	6832.7	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 11.55 ± 1.0 kcal/mol	Ruscic CBS-n
0.9	6832.4	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 10.77 ± 1.0 kcal/mol	Ruscic G4
0.8	6838.2	3 HCCH (g) → HCCCCCCH (g) + 2 H2 (g)	Δ_rH°(0 K) = -2.33 ± 1.3 kcal/mol	Ruscic G4
0.7	9096.1	5 CH4 (g) → CHCCHCCH (g) + 17/2 H2 (g)	Δ_rH°(0 K) = 910.05 ± 2.00 kJ/mol	Klippenstein 2017
0.7	6831.3	HCCCCH (g) + 2 CH4 (g) → CH3CH3 (g) + 2 HCCH (g)	Δ_rH°(0 K) = 16.02 ± 1.1 kcal/mol	Ruscic G3X

Top 10 species with enthalpies of formation correlated to the Δ_fH° of HCCCCH (g)

Please note: The correlation coefficients are obtained by renormalizing the off-diagonal elements of the covariance matrix by the corresponding variances.
The correlation coefficient is a number from -1 to 1, with 1 representing perfectly correlated species, -1 representing perfectly anti-correlated species, and 0 representing perfectly uncorrelated species.

Correlation Coefficent (%)	Species Name	Formula	Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units	Relative Molecular Mass	ATcT ID
87.2	1,3-Butadiyne cation	[HCCCCH]+ (g)	1440.21	1442.07	± 0.55	kJ/mol	50.0581 ± 0.0032	55468-55-8*0
52.6	1,3,5-Hexatriyne	HCCCCCCH (g)	682.1	686.9	± 1.2	kJ/mol	74.0801 ± 0.0048	3161-99-7*0
44.9	1,3-Pentadiyne	HCCCCCH3 (g)	418.16	413.94	± 0.65	kJ/mol	64.0853 ± 0.0040	4911-55-1*0
37.3	Butadiynyl	CCCCH (g)	801.86	808.46	± 0.96	kJ/mol	49.0507 ± 0.0032	53561-65-2*0
37.1	Diacetylide	[CCCCH]- (g)	460.94	465.98	± 0.96	kJ/mol	49.0513 ± 0.0032	59012-21-4*0
31.6	Cyanoacetylene	HCCCN (g)	372.22	373.96	± 0.57	kJ/mol	51.0468 ± 0.0024	1070-71-9*0
31.5	Cyanoacetylene cation	[HCCCN]+ (g)	1495.56	1497.86	± 0.57	kJ/mol	51.0462 ± 0.0024	85398-68-1*0
31.2	Acetylene	HCCH (g)	228.86	228.30	± 0.12	kJ/mol	26.0373 ± 0.0016	74-86-2*0
31.2	Acetylene cation	[HCCH]+ (g)	1328.88	1328.21	± 0.12	kJ/mol	26.0367 ± 0.0016	25641-79-6*0
27.8	2,4-Hexadiyne	CH3CCCCCH3 (g)	380.33	370.31	± 0.82	kJ/mol	78.1118 ± 0.0048	2809-69-0*0

Most Influential reactions involving HCCCCH (g)

Please note: The list, which is based on a hat (projection) matrix analysis, is limited to no more than 20 largest influences.

Influence Coefficient	TN ID	Reaction	Measured Quantity	Reference
0.554	6827.1	HCCCCH (g) → [HCCCCH]+ (g)	Δ_rH°(0 K) = 82064 ± 30 cm-1	Ramos 2002
0.311	6827.2	HCCCCH (g) → [HCCCCH]+ (g)	Δ_rH°(0 K) = 82108 ± 40 cm-1	Smith 1967, note unc
0.285	6847.4	HCCCCCCH (g) + CCCCH (g) → CCCCCCH (g) + HCCCCH (g)	Δ_rH°(0 K) = -5.72 ± 0.90 kcal/mol	Ruscic CBS-n
0.274	6837.6	HCCCCCCH (g) + HCCH (g) → 2 HCCCCH (g)	Δ_rH°(0 K) = 5.15 ± 2.00 kJ/mol	Klippenstein 2017
0.198	9274.6	HCCCCH (g) + CCH (g) → CCCCH (g) + HCCH (g)	Δ_rH°(0 K) = 9.81 ± 2.00 kJ/mol	Klippenstein 2017
0.198	9273.6	HCCCCH (g) → CCCCH (g) + H (g)	Δ_rH°(0 K) = 560.33 ± 2.00 kJ/mol	Klippenstein 2017
0.190	6915.9	C6H4 (g, singlet) → HCCCCH (g) + HCCH (g)	Δ_rH°(0 K) = 52.4 ± 0.5 kcal/mol	Zhang 2007
0.135	6830.10	2 HCCH (g) → HCCCCH (g) + H2 (g)	Δ_rH°(0 K) = 0.03 ± 0.3 kcal/mol	Simmonett 2009
0.107	8293.5	[CH2CCCH]+ (g, singlet) + HCCH (g) → HCCCCH (g) + [CH2CH]+ (g)	Δ_rH°(0 K) = 17.98 ± 0.8 kcal/mol	Ruscic W1RO
0.106	9041.5	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.47 ± 0.85 kcal/mol	Ruscic W1RO
0.094	9041.4	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.95 ± 0.90 kcal/mol	Ruscic CBS-n
0.094	9041.2	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.63 ± 0.90 kcal/mol	Ruscic G4
0.094	9041.1	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.63 ± 0.90 kcal/mol	Ruscic G3X
0.093	7980.5	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.72 ± 0.85 kcal/mol	Ruscic W1RO
0.093	7984.9	HCCCN (g) + HCCH (g) → HCCCCH (g) + HCN (g)	Δ_rH°(0 K) = -13.68 ± 2.0 kJ/mol	Klippenstein 2017
0.093	9040.6	HCCCCCH3 (g) + HCCH (g) → HCCCCH (g) + CH3CCH (g)	Δ_rH°(0 K) = 4.03 ± 2.00 kJ/mol	Klippenstein 2017
0.086	6837.5	HCCCCCCH (g) + HCCH (g) → 2 HCCCCH (g)	Δ_rH°(0 K) = 1.46 ± 0.85 kcal/mol	Ruscic W1RO
0.083	7980.1	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.94 ± 0.90 kcal/mol	Ruscic G3X
0.083	7980.2	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.61 ± 0.90 kcal/mol	Ruscic G4
0.083	7980.4	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.63 ± 0.90 kcal/mol	Ruscic CBS-n

References

1		B. Ruscic, R. E. Pinzon, M. L. Morton, G. von Laszewski, S. Bittner, S. G. Nijsure, K. A. Amin, M. Minkoff, and A. F. Wagner, Introduction to Active Thermochemical Tables: Several "Key" Enthalpies of Formation Revisited. J. Phys. Chem. A 108, 9979-9997 (2004) [DOI: 10.1021/jp047912y]
2		B. Ruscic, R. E. Pinzon, G. von Laszewski, D. Kodeboyina, A. Burcat, D. Leahy, D. Montoya, and A. F. Wagner, Active Thermochemical Tables: Thermochemistry for the 21^st Century. J. Phys. Conf. Ser. 16, 561-570 (2005) [DOI: 10.1088/1742-6596/16/1/078]
3		B. Ruscic and D. H. Bross, Active Thermochemical Tables (ATcT) values based on ver. 1.176 of the Thermochemical Network (2024); available at ATcT.anl.gov
4		T. L. Nguyen et al, ongoing studies (2024)
5		B. Ruscic, Uncertainty Quantification in Thermochemistry, Benchmarking Electronic Structure Computations, and Active Thermochemical Tables. Int. J. Quantum Chem. 114, 1097-1101 (2014) [DOI: 10.1002/qua.24605]
6		B. Ruscic and D. H. Bross, Thermochemistry Computer Aided Chem. Eng. 45, 3-114 (2019) [DOI: 10.1016/B978-0-444-64087-1.00001-2]

Formula

The aggregate state is given in parentheses following the formula, such as: g - gas-phase, cr - crystal, l - liquid, etc.

Uncertainties

The listed uncertainties correspond to estimated 95% confidence limits, as customary in thermochemistry (see, for example, Ruscic [5] and Ruscic and Bross[6]).
Note that an uncertainty of ± 0.000 kJ/mol indicates that the estimated uncertainty is < ± 0.000₅ kJ/mol.

Website Functionality Credits

The reorganization of the website was developed and implemented by David H. Bross (ANL).
The find function is based on the complete Species Dictionary entries for the appropriate version of the ATcT TN.
The molecule images are rendered by Indigo-depict.
The XYZ renderings are based on Jmol: an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/.

Acknowledgement

This work was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences and Biosciences under Contract No. DE-AC02-06CH11357.