Selected ATcT [1, 2] enthalpy of formation based on version 1.156 of the Thermochemical Network [3]

This version of ATcT results[3] was generated by additional expansion of version 1.148 to include species relevant to a recent study of the oxidation of ethylene [4] as well as new measurements that led to refining the thermochemistry of CF and SiF and their cations [5].

Cyclobutene

Formula: CH2(CH2CHCH) (g)

CAS RN: 822-35-5

ATcT ID: 822-35-5*0

SMILES: C1CC=C1

InChI: InChI=1S/C4H6/c1-2-4-3-1/h1-2H,3-4H2

InChIKey: CFBGXYDUODCMNS-UHFFFAOYSA-N

Hills Formula: C4H6

2D Image:

Aliases: CH2(CH2CHCH); Cyclobutene; cyc-C4H6; c-C4H6; CH2(CHCHCH2); CH(CH2CH2CH); CH(CHCH2CH2)

Relative Molecular Mass: 54.0904 ± 0.0032

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
178.04	161.00	± 0.60	kJ/mol

3D Image of CH2(CH2CHCH) (g)

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Top contributors to the provenance of Δ_fH° of CH2(CH2CHCH) (g)

The 20 contributors listed below account only for 74.2% of the provenance of Δ_fH° of CH2(CH2CHCH) (g).
A total of 41 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
13.0	3776.8	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.53 ± 0.35 kcal/mol	Karton 2017
10.0	3776.7	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.26 ± 0.4 kcal/mol	Karton 2009a
9.2	3773.8	CH2(CH2CHCH) (g) → 4 C (g) + 6 H (g)	Δ_rH°(0 K) = 947.17 ± 0.45 kcal/mol	Karton 2017
8.3	3774.1	4 CH4 (g) → CH2(CH2CHCH) (g) + 5 H2 (g)	Δ_rH°(0 K) = 443.94 ± 2.00 kJ/mol	Klippenstein 2017
6.9	3790.6	CH3CHCCH2 (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = 1.53 ± 2.00 kJ/mol	Klippenstein 2017
6.5	8012.1	CH(CHCHCH) (g) + H2 (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = -257.12 ± 2.00 kJ/mol	Klippenstein 2017
5.2	3773.7	CH2(CH2CHCH) (g) → 4 C (g) + 6 H (g)	Δ_rH°(0 K) = 947.76 ± 0.60 kcal/mol	Karton 2009a
1.9	3775.1	CH2(CH2CHCH) (g) + 11/2 O2 (g) → 4 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -618.60 ± 0.36 (×2.768) kcal/mol	Wiberg 1968, Fenoglio 1967
1.3	3776.6	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.06 ± 1.1 kcal/mol	Karton 2009a
1.1	3777.5	CH2(CH2CHCH) (g) → CH3CCCH3 (g)	Δ_rH°(0 K) = -4.11 ± 1.2 kcal/mol	Ruscic W1RO
1.1	3776.5	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.05 ± 1.2 kcal/mol	Ruscic W1RO
1.1	3792.1	CH3CHCCH2 (g) + 11/2 O2 (g) → 4 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -619.92 ± 0.13 kcal/mol	Prosen 1951
1.1	3790.5	CH3CHCCH2 (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = 0.12 ± 1.2 kcal/mol	Ruscic W1RO
1.1	3784.5	CH3CH2CCH (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = -0.91 ± 1.2 kcal/mol	Ruscic W1RO
1.0	3773.6	CH2(CH2CHCH) (g) → 4 C (g) + 6 H (g)	Δ_rH°(0 K) = 947.91 ± 1.35 kcal/mol	Karton 2009a
1.0	3760.1	CH2CHCHCH2 (g) + 2 H2 (g) → CH3CH2CH2CH3 (g)	Δ_rH°(355.15 K) = -57.079 ± 0.10 kcal/mol	Kistiakowsky 1936, Prosen 1945c
0.9	3777.2	CH2(CH2CHCH) (g) → CH3CCCH3 (g)	Δ_rH°(0 K) = -4.73 ± 1.3 kcal/mol	Ruscic G4
0.9	3777.4	CH2(CH2CHCH) (g) → CH3CCCH3 (g)	Δ_rH°(0 K) = -4.71 ± 1.3 kcal/mol	Ruscic CBS-n
0.9	3776.2	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.85 ± 1.3 kcal/mol	Ruscic G4
0.9	3776.4	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.09 ± 1.3 kcal/mol	Ruscic CBS-n

Top 10 species with enthalpies of formation correlated to the Δ_fH° of CH2(CH2CHCH) (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
23.8	1,3-Butadiene	CH2CHCHCH2 (g)	125.61	111.14	± 0.29	kJ/mol	54.0904 ± 0.0032	106-99-0*0
16.4	1,2-Butadiene	CH3CHCCH2 (g)	176.04	162.55	± 0.42	kJ/mol	54.0904 ± 0.0032	590-19-2*0
15.1	Carbon	C (g, singlet)	833.331	838.477	± 0.040	kJ/mol	12.01070 ± 0.00080	7440-44-0*2
15.1	Carbon	C (g, quintuplet)	1114.963	1120.109	± 0.040	kJ/mol	12.01070 ± 0.00080	7440-44-0*3
15.1	Carbon cation	C+ (g)	1797.853	1803.451	± 0.040	kJ/mol	12.01015 ± 0.00080	14067-05-1*0
15.1	Carbon	C (g, triplet)	711.400	716.885	± 0.040	kJ/mol	12.01070 ± 0.00080	7440-44-0*1
15.1	Carbon	C (g)	711.400	716.885	± 0.040	kJ/mol	12.01070 ± 0.00080	7440-44-0*0
15.1	Carbon dication	[C]+2 (g)	4150.469	4155.616	± 0.040	kJ/mol	12.00960 ± 0.00080	16092-61-8*0
15.0	Carbon anion	C- (g)	589.624	594.770	± 0.040	kJ/mol	12.01125 ± 0.00080	14337-00-9*0
14.9	Methyliumylidene	[CH]+ (g)	1619.757	1623.100	± 0.041	kJ/mol	13.01809 ± 0.00080	24361-82-8*0

Most Influential reactions involving CH2(CH2CHCH) (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
0.167	3776.8	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.53 ± 0.35 kcal/mol	Karton 2017
0.160	8012.1	CH(CHCHCH) (g) + H2 (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = -257.12 ± 2.00 kJ/mol	Klippenstein 2017
0.128	3776.7	CH2(CH2CHCH) (g) → CH2CHCHCH2 (g)	Δ_rH°(0 K) = -12.26 ± 0.4 kcal/mol	Karton 2009a
0.112	3790.6	CH3CHCCH2 (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = 1.53 ± 2.00 kJ/mol	Klippenstein 2017
0.099	3773.8	CH2(CH2CHCH) (g) → 4 C (g) + 6 H (g)	Δ_rH°(0 K) = 947.17 ± 0.45 kcal/mol	Karton 2017
0.090	3774.1	4 CH4 (g) → CH2(CH2CHCH) (g) + 5 H2 (g)	Δ_rH°(0 K) = 443.94 ± 2.00 kJ/mol	Klippenstein 2017
0.056	3773.7	CH2(CH2CHCH) (g) → 4 C (g) + 6 H (g)	Δ_rH°(0 K) = 947.76 ± 0.60 kcal/mol	Karton 2009a
0.055	8226.6	CH2(CH2CHCH) (g) → CH2(CHCHCH) (g) + H (g)	Δ_rH°(0 K) = 380.49 ± 2.00 (×2.65) kJ/mol	Klippenstein 2017
0.039	8226.5	CH2(CH2CHCH) (g) → CH2(CHCHCH) (g) + H (g)	Δ_rH°(0 K) = 89.75 ± 1.50 kcal/mol	Ruscic W1RO
0.034	8226.2	CH2(CH2CHCH) (g) → CH2(CHCHCH) (g) + H (g)	Δ_rH°(0 K) = 88.81 ± 1.60 kcal/mol	Ruscic G4
0.034	8226.4	CH2(CH2CHCH) (g) → CH2(CHCHCH) (g) + H (g)	Δ_rH°(0 K) = 89.47 ± 1.60 kcal/mol	Ruscic CBS-n
0.030	8226.1	CH2(CH2CHCH) (g) → CH2(CHCHCH) (g) + H (g)	Δ_rH°(0 K) = 89.40 ± 1.72 kcal/mol	Ruscic G3X
0.023	3784.5	CH3CH2CCH (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = -0.91 ± 1.2 kcal/mol	Ruscic W1RO
0.020	8782.5	CH(CH2CH2CH2) (g) → CH2(CH2CHCH) (g) + H (g)	Δ_rH°(0 K) = 35.61 ± 1.50 kcal/mol	Ruscic W1RO
0.020	3775.1	CH2(CH2CHCH) (g) + 11/2 O2 (g) → 4 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -618.60 ± 0.36 (×2.768) kcal/mol	Wiberg 1968, Fenoglio 1967
0.019	3784.4	CH3CH2CCH (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = -0.60 ± 1.3 kcal/mol	Ruscic CBS-n
0.019	3784.2	CH3CH2CCH (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = -0.25 ± 1.3 kcal/mol	Ruscic G4
0.019	3777.5	CH2(CH2CHCH) (g) → CH3CCCH3 (g)	Δ_rH°(0 K) = -4.11 ± 1.2 kcal/mol	Ruscic W1RO
0.019	8226.3	CH2(CH2CHCH) (g) → CH2(CHCHCH) (g) + H (g)	Δ_rH°(0 K) = 89.23 ± 2.16 kcal/mol	Ruscic CBS-n
0.017	3790.5	CH3CHCCH2 (g) → CH2(CH2CHCH) (g)	Δ_rH°(0 K) = 0.12 ± 1.2 kcal/mol	Ruscic W1RO

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. 1.156 of the Thermochemical Network (2024); available at ATcT.anl.gov
4		N. A. Seifert, B. Ruscic, R. Sivaramakrishnan, and K. Prozument, The C2H4O Isomers in the Oxidation of Ethylene J. Mol. Spectrosc. 398, 111847/1-8 (2023) [DOI: 10.1016/j.jms.2023.111847]
5		U. Jacovella, B. Ruscic, N. L. Chen, H.-L. Le, S. Boyé-Péronne, S. Hartweg, M. Roy-Chowdhury, G. A. Garcia, J.-C. Loison, and B. Gans, Refining Thermochemical Properties of CF, SiF, and Their Cations by Combining Photoelectron Spectroscopy, Quantum Chemical Calculations, and the Active Thermochemical Tables Approach Phys. Chem. Chem. Phys. 25, 30838-30847 (2023) [DOI: 10.1039/D3CP04244H]
6		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]
7		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] and Ruscic and Bross[7]).
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.