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-Dioxolan-2-one

Formula: C(O)(OCH2CH2O) (g)

CAS RN: 96-49-1

ATcT ID: 96-49-1*0

SMILES: C1(=O)OCCO1

InChI: InChI=1S/C3H4O3/c4-3-5-1-2-6-3/h1-2H2

InChIKey: KMTRUDSVKNLOMY-UHFFFAOYSA-N

Hills Formula: C3H4O3

2D Image:

Aliases: C(O)(OCH2CH2O); 1,3-Dioxolan-2-one; Ethylene carbonate; Cyclic carbonic acid ethylene ester; Cyclic ethylene carbonate; Cyclic ethylene glycol carbonste; Ethylene glycol carbonate; Glycol carbonate; 2-Dioxolone; Dioxolone-2; 1,3-Dioxacyclopentan-2-one; Texacar EC; NSC 11801; OC(OCH2CH2O)

Relative Molecular Mass: 88.0621 ± 0.0026

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
-492.62	-510.27	± 0.85	kJ/mol

Top contributors to the provenance of Δ_fH° of C(O)(OCH2CH2O) (g)

The 20 contributors listed below account only for 79.0% of the provenance of Δ_fH° of C(O)(OCH2CH2O) (g).
A total of 29 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
10.3	3224.2	C(O)(OCH2CH2O) (cr,l) → C(O)(OCH2CH2O) (g)	Δ_rH°(298.15 K) = 17.5 ± 0.6 kcal/mol	Peppel 1958, Cox 1970
8.0	3224.1	C(O)(OCH2CH2O) (cr,l) → C(O)(OCH2CH2O) (g)	Δ_rH°(298.15 K) = 74.1 ± 1.2 (×2.378) kJ/mol	Verevkin 2008, note unc
4.5	3234.5	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.48 ± 0.85 kcal/mol	Ruscic W1RO
4.0	3234.2	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.85 ± 0.90 kcal/mol	Ruscic G4
4.0	3234.4	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.81 ± 0.90 kcal/mol	Ruscic CBS-n
4.0	3234.1	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.64 ± 0.90 kcal/mol	Ruscic G3X
3.9	3226.5	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.32 ± 0.85 kcal/mol	Ruscic W1RO
3.7	3235.5	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.63 ± 0.85 kcal/mol	Ruscic W1RO
3.5	3226.4	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.98 ± 0.90 kcal/mol	Ruscic CBS-n
3.5	3226.2	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.12 ± 0.90 kcal/mol	Ruscic G4
3.5	3226.1	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 22.01 ± 0.90 kcal/mol	Ruscic G3X
3.3	3235.2	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.11 ± 0.90 kcal/mol	Ruscic G4
3.3	3235.4	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.81 ± 0.90 kcal/mol	Ruscic CBS-n
3.3	3235.1	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.36 ± 0.90 kcal/mol	Ruscic G3X
3.2	3234.3	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.80 ± 1.00 kcal/mol	Ruscic CBS-n
2.9	3231.1	C(O)(OCH3)2 (cr,l) + 3 O2 (g) → 3 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -1429.28 ± 0.30 kJ/mol	Steele 1997a
2.8	3226.3	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.86 ± 1.00 kcal/mol	Ruscic CBS-n
2.6	3235.3	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.55 ± 1.00 kcal/mol	Ruscic CBS-n
2.0	3225.5	C(O)(OCH2CH2O) (g) → CH3C(O)C(O)OH (g)	Δ_rH°(0 K) = -6.34 ± 1.2 kcal/mol	Ruscic W1RO
1.7	3225.4	C(O)(OCH2CH2O) (g) → CH3C(O)C(O)OH (g)	Δ_rH°(0 K) = -5.76 ± 1.3 kcal/mol	Ruscic CBS-n

Top 10 species with enthalpies of formation correlated to the Δ_fH° of C(O)(OCH2CH2O) (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
22.9	Dimethyl carbonate	C(O)(OCH3)2 (g, cis-cis)	-550.04	-570.59	± 0.37	kJ/mol	90.0779 ± 0.0026	616-38-6*1
22.9	Dimethyl carbonate	C(O)(OCH3)2 (g)	-550.04	-570.47	± 0.37	kJ/mol	90.0779 ± 0.0026	616-38-6*0
18.9	Dimethyl carbonate	C(O)(OCH3)2 (cr,l)		-608.60	± 0.31	kJ/mol	90.0779 ± 0.0026	616-38-6*500
17.0	Oxirane	O(CH2CH2) (g)	-39.73	-52.29	± 0.33	kJ/mol	44.0526 ± 0.0017	75-21-8*0
15.0	Carbonic acid	C(O)(OH)2 (g)	-602.29	-611.60	± 0.55	kJ/mol	62.0248 ± 0.0012	463-79-6*0
15.0	Carbonic acid	C(O)(OH)2 (g, cis-cis)	-602.29	-612.46	± 0.55	kJ/mol	62.0248 ± 0.0012	463-79-6*1
13.3	Pyruvic acid	CH3C(O)C(O)OH (g)	-520.58	-534.92	± 0.97	kJ/mol	88.0621 ± 0.0026	127-17-3*0
10.0	1,3-Dioxolan-2-one	C(O)(OCH2CH2O) (cr,l)		-581.53	± 0.36	kJ/mol	88.0621 ± 0.0026	96-49-1*500
9.3	Oxirane	O(CH2CH2) (cr,l)	-77.13	-77.80	± 0.60	kJ/mol	44.0526 ± 0.0017	75-21-8*500
8.9	Methyl hydrocarbonate	C(O)(OH)OCH3 (g, cis-cis)	-577.04	-592.59	± 0.87	kJ/mol	76.0514 ± 0.0019	7456-87-3*1

Most Influential reactions involving C(O)(OCH2CH2O) (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
0.124	3224.2	C(O)(OCH2CH2O) (cr,l) → C(O)(OCH2CH2O) (g)	Δ_rH°(298.15 K) = 17.5 ± 0.6 kcal/mol	Peppel 1958, Cox 1970
0.096	3224.1	C(O)(OCH2CH2O) (cr,l) → C(O)(OCH2CH2O) (g)	Δ_rH°(298.15 K) = 74.1 ± 1.2 (×2.378) kJ/mol	Verevkin 2008, note unc
0.069	3226.5	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.32 ± 0.85 kcal/mol	Ruscic W1RO
0.062	3226.2	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.12 ± 0.90 kcal/mol	Ruscic G4
0.062	3226.1	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 22.01 ± 0.90 kcal/mol	Ruscic G3X
0.062	3226.4	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.98 ± 0.90 kcal/mol	Ruscic CBS-n
0.061	3235.5	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.63 ± 0.85 kcal/mol	Ruscic W1RO
0.056	3225.5	C(O)(OCH2CH2O) (g) → CH3C(O)C(O)OH (g)	Δ_rH°(0 K) = -6.34 ± 1.2 kcal/mol	Ruscic W1RO
0.056	3234.5	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.48 ± 0.85 kcal/mol	Ruscic W1RO
0.054	3235.1	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.36 ± 0.90 kcal/mol	Ruscic G3X
0.054	3235.4	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.81 ± 0.90 kcal/mol	Ruscic CBS-n
0.054	3235.2	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.11 ± 0.90 kcal/mol	Ruscic G4
0.050	3234.1	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.64 ± 0.90 kcal/mol	Ruscic G3X
0.050	3234.4	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.81 ± 0.90 kcal/mol	Ruscic CBS-n
0.050	3234.2	C(O)(OCH3)2 (g, cis-cis) + CH3CH3 (g) → C(O)(OCH2CH2O) (g) + 2 CH4 (g)	Δ_rH°(0 K) = -1.85 ± 0.90 kcal/mol	Ruscic G4
0.050	3226.3	C(O)(OCH2CH2O) (g) + H2O (g) → C(O)(OH)2 (g, cis-cis) + O(CH2CH2) (g)	Δ_rH°(0 K) = 21.86 ± 1.00 kcal/mol	Ruscic CBS-n
0.048	3225.2	C(O)(OCH2CH2O) (g) → CH3C(O)C(O)OH (g)	Δ_rH°(0 K) = -5.90 ± 1.3 kcal/mol	Ruscic G4
0.048	3225.4	C(O)(OCH2CH2O) (g) → CH3C(O)C(O)OH (g)	Δ_rH°(0 K) = -5.76 ± 1.3 kcal/mol	Ruscic CBS-n
0.044	3235.3	C(O)(OCH3)2 (g, cis-cis) + O(CH2CH2) (g) → C(O)(OCH2CH2O) (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -16.55 ± 1.00 kcal/mol	Ruscic CBS-n
0.041	3225.1	C(O)(OCH2CH2O) (g) → CH3C(O)C(O)OH (g)	Δ_rH°(0 K) = -6.15 ± 1.4 kcal/mol	Ruscic G3X

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.