Selected ATcT [1, 2] enthalpy of formation based on version 1.130 of the Thermochemical Network [3]

This version of ATcT results[4] was generated by additional expansion of version 1.128 [5,6] to include with the calculations provided in reference [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
458.31	460.03	± 0.56	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 48.6% of the provenance of Δ_fH° of HCCCCH (g).
A total of 316 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
15.4	6484.10	2 HCCH (g) → HCCCCH (g) + H2 (g)	Δ_rH°(0 K) = 0.03 ± 0.3 kcal/mol	Simmonett 2009
7.1	6483.1	4 CH4 (g) → HCCCCH (g) + 7 H2 (g)	Δ_rH°(0 K) = 724.15 ± 2.00 kJ/mol	Klippenstein 2017
4.2	6550.9	C6H4 (g, singlet) → HCCCCH (g) + HCCH (g)	Δ_rH°(0 K) = 52.4 ± 0.5 kcal/mol	Zhang 2007
3.6	8586.1	4 CH4 (g) → CCCCH (g) + 15/2 H2 (g)	Δ_rH°(0 K) = 1068.39 ± 2.00 kJ/mol	Klippenstein 2017
2.6	7464.9	HCCCN (g) + HCCH (g) → HCCCCH (g) + HCN (g)	Δ_rH°(0 K) = -13.68 ± 2.0 kJ/mol	Klippenstein 2017
1.7	6485.8	HCCCCH (g) + 2 CH4 (g) → CH3CH3 (g) + 2 HCCH (g)	Δ_rH°(0 K) = 15.07 ± 0.9 kcal/mol	Ruscic W1RO
1.6	6486.8	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 11.48 ± 0.9 kcal/mol	Ruscic W1RO
1.3	6485.4	HCCCCH (g) + 2 CH4 (g) → CH3CH3 (g) + 2 HCCH (g)	Δ_rH°(0 K) = 15.68 ± 1.0 kcal/mol	Ruscic G4
1.3	6486.4	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 10.77 ± 1.0 kcal/mol	Ruscic G4
1.3	6486.7	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 11.55 ± 1.0 kcal/mol	Ruscic CBS-n
1.1	6485.3	HCCCCH (g) + 2 CH4 (g) → CH3CH3 (g) + 2 HCCH (g)	Δ_rH°(0 K) = 16.02 ± 1.1 kcal/mol	Ruscic G3X
0.9	6484.8	2 HCCH (g) → HCCCCH (g) + H2 (g)	Δ_rH°(0 K) = 0.17 ± 1.2 kcal/mol	Ruscic W1RO
0.8	6484.4	2 HCCH (g) → HCCCCH (g) + H2 (g)	Δ_rH°(0 K) = -0.33 ± 1.3 kcal/mol	Ruscic G4
0.8	6485.6	HCCCCH (g) + 2 CH4 (g) → CH3CH3 (g) + 2 HCCH (g)	Δ_rH°(0 K) = 16.09 ± 1.3 kcal/mol	Ruscic CBS-n
0.7	6486.6	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 10.92 ± 1.3 kcal/mol	Ruscic CBS-n
0.7	6486.3	HCCCCH (g) + 2 HCN (g) → NCCN (g) + 2 HCCH (g)	Δ_rH°(0 K) = 10.20 ± 1.1 (×1.215) kcal/mol	Ruscic G3X
0.7	7464.8	HCCCN (g) + HCCH (g) → HCCCCH (g) + HCN (g)	Δ_rH°(0 K) = -3.38 ± 0.9 kcal/mol	Ruscic W1RO
0.7	8517.5	C6H4(C4H4) (g) → C6H6 (g) + HCCCCH (g)	Δ_rH°(0 K) = 93.00 ± 1.50 kcal/mol	Ruscic W1RO
0.7	6484.3	2 HCCH (g) → HCCCCH (g) + H2 (g)	Δ_rH°(0 K) = -0.73 ± 1.4 kcal/mol	Ruscic G3X
0.6	6480.8	HCCCCH (g) → 2 H (g) + 4 C (g)	Δ_rH°(0 K) = 673.74 ± 1.50 kcal/mol	Ruscic W1RO

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
89.9	1,3-Butadiyne cation	[HCCCCH]+ (g)	1440.16	1442.03	± 0.62	kJ/mol	50.0581 ± 0.0032	55468-55-8*0
51.7	1,3-Pentadiyne	HCCCCCH3 (g)	417.98	413.76	± 0.83	kJ/mol	64.0853 ± 0.0040	4911-55-1*0
40.8	Butadiynyl	CCCCH (g)	801.72	808.32	± 0.99	kJ/mol	49.0507 ± 0.0032	53561-65-2*0
40.6	Diacetylide	[CCCCH]- (g)	460.8	465.8	± 1.0	kJ/mol	49.0513 ± 0.0032	59012-21-4*0
35.8	Cyanoacetylene	HCCCN (g)	372.19	373.93	± 0.59	kJ/mol	51.0468 ± 0.0024	1070-71-9*0
35.7	Cyanoacetylene cation	[HCCCN]+ (g)	1495.52	1497.82	± 0.59	kJ/mol	51.0462 ± 0.0024	85398-68-1*0
35.2	2,4-Hexadiyne	CH3CCCCCH3 (g)	380.17	370.15	± 0.86	kJ/mol	78.1118 ± 0.0048	2809-69-0*0
32.4	1,3-Hexadiyne	HCCCCCH2CH3 (g)	405.10	393.41	± 0.97	kJ/mol	78.1118 ± 0.0048	4447-21-6*0
30.6	2,4-Hexadiyne	CH3CCCCCH3 (cr,l)	319.00	312.64	± 0.99	kJ/mol	78.1118 ± 0.0048	2809-69-0*500
25.6	Acetylene	HCCH (g)	228.88	228.32	± 0.12	kJ/mol	26.0373 ± 0.0016	74-86-2*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	6481.1	HCCCCH (g) → [HCCCCH]+ (g)	Δ_rH°(0 K) = 82064 ± 30 cm-1	Ramos 2002
0.311	6481.2	HCCCCH (g) → [HCCCCH]+ (g)	Δ_rH°(0 K) = 82108 ± 40 cm-1	Smith 1967, note unc
0.209	8588.6	HCCCCH (g) + CCH (g) → CCCCH (g) + HCCH (g)	Δ_rH°(0 K) = 9.81 ± 2.00 kJ/mol	Klippenstein 2017
0.209	8587.6	HCCCCH (g) → CCCCH (g) + H (g)	Δ_rH°(0 K) = 560.33 ± 2.00 kJ/mol	Klippenstein 2017
0.201	6550.9	C6H4 (g, singlet) → HCCCCH (g) + HCCH (g)	Δ_rH°(0 K) = 52.4 ± 0.5 kcal/mol	Zhang 2007
0.188	6484.10	2 HCCH (g) → HCCCCH (g) + H2 (g)	Δ_rH°(0 K) = 0.03 ± 0.3 kcal/mol	Simmonett 2009
0.138	8417.5	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.47 ± 0.85 kcal/mol	Ruscic W1RO
0.123	8417.2	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.63 ± 0.90 kcal/mol	Ruscic G4
0.123	8417.4	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.95 ± 0.90 kcal/mol	Ruscic CBS-n
0.123	8417.1	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.63 ± 0.90 kcal/mol	Ruscic G3X
0.111	7773.5	[CH2CCCH]+ (g, singlet) + HCCH (g) → HCCCCH (g) + [CH2CH]+ (g)	Δ_rH°(0 K) = 17.98 ± 0.8 kcal/mol	Ruscic W1RO
0.104	7464.9	HCCCN (g) + HCCH (g) → HCCCCH (g) + HCN (g)	Δ_rH°(0 K) = -13.68 ± 2.0 kJ/mol	Klippenstein 2017
0.100	8417.3	2 HCCCCCH3 (g) → HCCCCH (g) + CH3CCCCCH3 (g)	Δ_rH°(0 K) = 0.44 ± 1.0 kcal/mol	Ruscic CBS-n
0.097	7460.5	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.72 ± 0.85 kcal/mol	Ruscic W1RO
0.087	7460.4	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.63 ± 0.90 kcal/mol	Ruscic CBS-n
0.087	7460.2	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.61 ± 0.90 kcal/mol	Ruscic G4
0.087	7460.1	2 HCCCN (g) → HCCCCH (g) + NCCN (g)	Δ_rH°(0 K) = 4.94 ± 0.90 kcal/mol	Ruscic G3X
0.080	7772.5	[CH2CCCH]+ (g, singlet) → HCCCCH (g) + H+ (g)	Δ_rH°(0 K) = 170.99 ± 0.90 kcal/mol	Ruscic W1RO
0.078	6483.1	4 CH4 (g) → HCCCCH (g) + 7 H2 (g)	Δ_rH°(0 K) = 724.15 ± 2.00 kJ/mol	Klippenstein 2017
0.076	6481.3	HCCCCH (g) → [HCCCCH]+ (g)	Δ_rH°(0 K) = 10.17 ± 0.01 eV	Baker 1968, Baker 1967, Bieri 1977

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. 1.130 of the Thermochemical Network. Argonne National Laboratory, Lemont, Illinois 2023; available at ATcT.anl.gov [DOI: 10.17038/CSE/1997229]
4		N. Genossar, P. B. Changala, B. Gans, J.-C. Loison, S. Hartweg, M.-A. Martin-Drumel, G. A. Garcia, J. F. Stanton, B. Ruscic, and J. H. Baraban Ring-Opening Dynamics of the Cyclopropyl Radical and Cation: the Transition State Nature of the Cyclopropyl Cation J. Am. Chem. Soc. 144, 18518-18525 (2022) [DOI: 10.1021/jacs.2c07740]
5		B. Ruscic and D. H. Bross Active Thermochemical Tables: The Thermophysical and Thermochemical Properties of Methyl, CH3, and Methylene, CH2, Corrected for Nonrigid Rotor and Anharmonic Oscillator Effects. Mol. Phys. e1969046 (2021) [DOI: 10.1080/00268976.2021.1969046]
6		J. H. Thorpe, J. L. Kilburn, D. Feller, P. B. Changala, D. H. Bross, B. Ruscic, and J. F. Stanton, Elaborated Thermochemical Treatment of HF, CO, N2, and H2O: Insight into HEAT and Its Extensions J. Chem. Phys. 155, 184109 (2021) [DOI: 10.1063/5.0069322]
7		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]
8		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 [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.