Selected ATcT [1, 2] enthalpy of formation based on version 1.172 of the Thermochemical Network [3]

This version of ATcT results[3] was generated by additional expansion of version 1.156 to include species relevant to a study of photodissociation of formamide[4].

Vinylacetylene

Formula: CH2CHCCH (g)

CAS RN: 689-97-4

ATcT ID: 689-97-4*0

SMILES: C=CC#C

InChI: InChI=1S/C4H4/c1-3-4-2/h1,4H,2H2

InChIKey: WFYPICNXBKQZGB-UHFFFAOYSA-N

Hills Formula: C4H4

2D Image:

Aliases: CH2CHCCH; Vinylacetylene; But-1-en-3-yne; 1-Buten-3-yne; Butenyne; 1-Butenyne; 1-Butyn-3-ene; 3-Buten-1-yne; 3-Butyn-1-ene; Ethynylethene; Monovinylacetylene; Vinylethyne; HCCCHCH2

Relative Molecular Mass: 52.0746 ± 0.0032

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
296.44	289.68	± 0.52	kJ/mol

3D Image of CH2CHCCH (g)

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Top contributors to the provenance of Δ_fH° of CH2CHCCH (g)

The 20 contributors listed below account only for 52.8% of the provenance of Δ_fH° of CH2CHCCH (g).
A total of 245 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
6.1	8130.1	4 CH4 (g) → CH2CHCCH (g) + 6 H2 (g)	Δ_rH°(0 K) = 561.94 ± 2.0 kJ/mol	Klippenstein 2017
6.0	8131.6	CH2CHCCH (g) + 3 H2 (g) → CH3CH2CH2CH3 (g)	Δ_rH°(0 K) = -394.18 ± 2.0 kJ/mol	Klippenstein 2017
5.4	8132.6	CH2CHCCH (g) + CH4 (g) → CH2CH2 (g) + CH3CCH (g)	Δ_rH°(0 K) = 23.34 ± 2.0 kJ/mol	Klippenstein 2017
5.4	8133.7	CH2CHCCH (g) + CH3CH3 (g) → CH3CCH (g) + CH3CHCH2 (g)	Δ_rH°(0 K) = -0.05 ± 2.00 kJ/mol	Klippenstein 2017
4.9	8133.6	CH2CHCCH (g) + CH3CH3 (g) → CH3CCH (g) + CH3CHCH2 (g)	Δ_rH°(0 K) = -0.12 ± 0.50 kcal/mol	Wheeler 2004, est unc
3.3	8154.9	CH(CHCHCH) (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -139.12 ± 2.0 kJ/mol	Klippenstein 2017
2.6	8127.6	CH2CHCCH (g) → 4 C (g) + 4 H (g)	Δ_rH°(0 K) = 3410.9 ± 3.0 kJ/mol	Klopper 2010a
2.2	8140.9	CH2CCCH2 (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -31.93 ± 2.0 kJ/mol	Klippenstein 2017
2.1	8230.6	CH2CCCH (g) → 4 C (g) + 3 H (g)	Δ_rH°(0 K) = 715.82 ± 0.50 kcal/mol	Wheeler 2004, est unc
2.1	8154.8	CH(CHCHCH) (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -139.2 ± 2.5 kJ/mol	Klopper 2010a, est unc
1.7	8145.1	4 CH4 (g) → CH2C(CHCH) (g) + 6 H2 (g)	Δ_rH°(0 K) = 661.86 ± 2.0 kJ/mol	Klippenstein 2017
1.5	8132.5	CH2CHCCH (g) + CH4 (g) → CH2CH2 (g) + CH3CCH (g)	Δ_rH°(0 K) = 5.40 ± 0.9 kcal/mol	Ruscic W1RO
1.4	8140.8	CH2CCCH2 (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -31.5 ± 2.5 kJ/mol	Klopper 2010a, est unc
1.3	8146.8	CH2C(CHCH) (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -99.92 ± 2.0 kJ/mol	Klippenstein 2017
1.2	8132.2	CH2CHCCH (g) + CH4 (g) → CH2CH2 (g) + CH3CCH (g)	Δ_rH°(0 K) = 5.72 ± 1.0 kcal/mol	Ruscic G4
1.2	8132.4	CH2CHCCH (g) + CH4 (g) → CH2CH2 (g) + CH3CCH (g)	Δ_rH°(0 K) = 5.86 ± 1.0 kcal/mol	Ruscic CBS-n
1.1	9006.6	CH2CCCCH2 (g) + CH2CCH2 (g) → 2 CH2CCCH2 (g)	Δ_rH°(0 K) = 6.45 ± 2.00 kJ/mol	Klippenstein 2017
1.0	8132.1	CH2CHCCH (g) + CH4 (g) → CH2CH2 (g) + CH3CCH (g)	Δ_rH°(0 K) = 5.72 ± 1.1 kcal/mol	Ruscic G3X
0.8	8241.7	CH2CHCCH (g) → CH2CCCH (g) + H (g)	Δ_rH°(0 K) = 416.05 ± 2.00 kJ/mol	Klippenstein 2017
0.8	8242.7	CH2CCCH (g) + CH4 (g) → CH2CHCCH (g) + CH3 (g)	Δ_rH°(0 K) = 16.53 ± 2.00 kJ/mol	Klippenstein 2017

Top 10 species with enthalpies of formation correlated to the Δ_fH° of CH2CHCCH (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
51.5	1,2,3-Butatrien-1-yl	CH2CCCH (g)	497.52	497.54	± 0.66	kJ/mol	51.0666 ± 0.0032	22112-56-7*0
44.4	1-Buten-3-yn-1-yl	HCCCHCH (g, trans)	547.36	544.70	± 0.84	kJ/mol	51.0666 ± 0.0032	2810-61-9*1
44.4	1-Buten-3-yn-1-yl	HCCCHCH (g)	547.36	544.85	± 0.84	kJ/mol	51.0666 ± 0.0032	2810-61-9*0
42.2	Butatriene	CH2CCCH2 (g)	328.40	322.14	± 0.53	kJ/mol	52.0746 ± 0.0032	2873-50-9*0
41.0	3-Buten-1-ynyl	CH2CHCC (g)	628.61	626.42	± 0.99	kJ/mol	51.0666 ± 0.0032	108179-98-2*0
38.2	Vinylacetylene cation	[CH2CHCCH]+ (g)	1221.8	1215.3	± 1.1	kJ/mol	52.0740 ± 0.0032	59699-48-8*0
37.1	But-1-en-3-yn-1-ide	[HCCCHCH]- (g, cis)	419.8	418.7	± 1.2	kJ/mol	51.0672 ± 0.0032	119611-65-3*2
37.1	But-1-en-3-yn-1-ide	[HCCCHCH]- (g)	419.8	419.2	± 1.2	kJ/mol	51.0672 ± 0.0032	119611-65-3*0
36.6	But-1-en-3-yn-1-ide	[HCCCHCH]- (g, trans)	422.5	421.1	± 1.3	kJ/mol	51.0672 ± 0.0032	119611-65-3*1
35.8	3-Methylenecyclopropene	CH2C(CHCH) (g)	396.08	388.15	± 0.81	kJ/mol	52.0746 ± 0.0032	4095-06-1*0

Most Influential reactions involving CH2CHCCH (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
0.997	8135.1	CH2CHCCH (cr,l) → CH2CHCCH (g)	Δ_rH°(298.15 K) = 23.13 ± 2 kJ/mol	ThermoData 2004, Stephenson 1987, est unc
0.257	8128.1	CH2CHCCH (g) → [CH2CHCCH]+ (g)	Δ_rH°(0 K) = 9.58 ± 0.02 eV	Bieri 1977
0.257	8128.2	CH2CHCCH (g) → [CH2CHCCH]+ (g)	Δ_rH°(0 K) = 9.58 ± 0.02 eV	Brogli 1975
0.155	8146.8	CH2C(CHCH) (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -99.92 ± 2.0 kJ/mol	Klippenstein 2017
0.131	8303.5	CH2CHCCH (g) + [CCH]- (g) → [CH2CHCC]- (g, singlet) + HCCH (g)	Δ_rH°(0 K) = -4.17 ± 0.8 kcal/mol	Ruscic W1RO
0.124	8154.9	CH(CHCHCH) (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -139.12 ± 2.0 kJ/mol	Klippenstein 2017
0.115	8278.5	CH2CHCCH (g) + [CH2CH]- (g) → [HCCCHCH]- (g, trans) + CH2CH2 (g)	Δ_rH°(0 K) = -11.93 ± 0.8 kcal/mol	Ruscic W1RO
0.107	8277.5	CH2CHCCH (g) + [CH2CH]- (g) → [HCCCHCH]- (g, cis) + CH2CH2 (g)	Δ_rH°(0 K) = -12.41 ± 0.8 kcal/mol	Ruscic W1RO
0.103	8302.5	CH2CHCCH (g) → [CH2CHCC]- (g, singlet) + H+ (g)	Δ_rH°(0 K) = 372.99 ± 0.90 kcal/mol	Ruscic W1RO
0.092	8276.5	CH2CHCCH (g) → [HCCCHCH]- (g, trans) + H+ (g)	Δ_rH°(0 K) = 395.58 ± 0.90 kcal/mol	Ruscic W1RO
0.087	8242.7	CH2CCCH (g) + CH4 (g) → CH2CHCCH (g) + CH3 (g)	Δ_rH°(0 K) = 16.53 ± 2.00 kJ/mol	Klippenstein 2017
0.087	8241.7	CH2CHCCH (g) → CH2CCCH (g) + H (g)	Δ_rH°(0 K) = 416.05 ± 2.00 kJ/mol	Klippenstein 2017
0.085	8275.5	CH2CHCCH (g) → [HCCCHCH]- (g, cis) + H+ (g)	Δ_rH°(0 K) = 395.10 ± 0.90 kcal/mol	Ruscic W1RO
0.083	8303.2	CH2CHCCH (g) + [CCH]- (g) → [CH2CHCC]- (g, singlet) + HCCH (g)	Δ_rH°(0 K) = -4.68 ± 1.0 kcal/mol	Ruscic G4
0.083	8303.4	CH2CHCCH (g) + [CCH]- (g) → [CH2CHCC]- (g, singlet) + HCCH (g)	Δ_rH°(0 K) = -4.46 ± 1.0 kcal/mol	Ruscic CBS-n
0.079	8154.8	CH(CHCHCH) (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -139.2 ± 2.5 kJ/mol	Klopper 2010a, est unc
0.079	8242.6	CH2CCCH (g) + CH4 (g) → CH2CHCCH (g) + CH3 (g)	Δ_rH°(0 K) = 3.20 ± 0.50 kcal/mol	Wheeler 2004, est unc
0.078	8140.9	CH2CCCH2 (g) → CH2CHCCH (g)	Δ_rH°(0 K) = -31.93 ± 2.0 kJ/mol	Klippenstein 2017
0.073	8278.4	CH2CHCCH (g) + [CH2CH]- (g) → [HCCCHCH]- (g, trans) + CH2CH2 (g)	Δ_rH°(0 K) = -11.73 ± 1.0 kcal/mol	Ruscic CBS-n
0.073	8278.2	CH2CHCCH (g) + [CH2CH]- (g) → [HCCCHCH]- (g, trans) + CH2CH2 (g)	Δ_rH°(0 K) = -12.25 ± 1.0 kcal/mol	Ruscic G4

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. 1.172 of the Thermochemical Network (2024); available at ATcT.anl.gov
4		K. L. Caster, N. A. Seifert, B. Ruscic, A. W. Jasper, and K. Prozument, Dynamics of HCN, NHC, and HNCO Formation in the 193 nm Photodissociation of Formamide J. Phys. Chem. A (in press) (2024) [DOI: 10.1021/acs.jpca.4c02232]
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.