Selected ATcT [1, 2] enthalpy of formation based on version 1.202 of the Thermochemical Network [3]

This version of ATcT results[3] was generated by additional expansion of version 1.176 in order to include species related to the thermochemistry of glycine[4].

Acetyl chloride

Formula: CH3C(O)Cl (l)

CAS RN: 75-36-5

ATcT ID: 75-36-5*500

SMILES: CC(=O)Cl

InChI: InChI=1S/C2H3ClO/c1-2(3)4/h1H3

InChIKey: WETWJCDKMRHUPV-UHFFFAOYSA-N

Hills Formula: C2H3Cl1O1

2D Image:

Aliases: CH3C(O)Cl; Acetyl chloride; Acetic acid chloride; Acetic chloride; Ethanoyl chloride; Methylcarbonyl chloride

Relative Molecular Mass: 78.4973 ± 0.0019

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
	-272.06	± 0.39	kJ/mol

Top contributors to the provenance of Δ_fH° of CH3C(O)Cl (l)

The 19 contributors listed below account for 90.1% of the provenance of Δ_fH° of CH3C(O)Cl (l).

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
22.7	5219.1	CH3C(O)Cl (l) + H2O (cr,l) → CH3C(O)OH (aq, 75 H2O) + HCl (aq, 75 H2O)	Δ_rH°(298.15 K) = -22.07 ± 0.07 kcal/mol	Carson 1949
17.2	5118.1	CH3C(O)OH (aq, 100 H2O) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.42 ± 0.20 kJ/mol	NBS Tables 1989, NBS TN270, Parker 1965
6.5	5114.2	CH3C(O)OH (cr,l) + 2 O2 (g) → 2 CO2 (g) + 2 H2O (cr,l)	Δ_rH°(298.15 K) = -209.125 ± 0.054 kcal/mol	Lebedeva 1964
5.7	5115.1	CH3C(O)OH (cr,l) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.360 ± 0.100 kcal/mol	Parker 1965, NBS Tables 1989, est unc
5.3	5220.1	CH3C(O)Cl (l) + H2O (cr,l) → CH3C(O)OH (aq, 1500 H2O) + HCl (aq, 1500 H2O)	Δ_rH°(298.15 K) = -22.22 ± 0.10 (×1.445) kcal/mol	Pritchard 1950, Parker 1965, NBS Tables 1989
3.5	5215.7	2 CH3C(O)Cl (g) + CH2O (g) → 2 CH3CHO (g) + CCl2O (g)	Δ_rH°(0 K) = 10.13 ± 0.9 kcal/mol	Ruscic W1RO
2.8	5114.3	CH3C(O)OH (cr,l) + 2 O2 (g) → 2 CO2 (g) + 2 H2O (cr,l)	Δ_rH°(298.15 K) = -875.14 ± 0.34 kJ/mol	Steele 1997
2.8	5215.4	2 CH3C(O)Cl (g) + CH2O (g) → 2 CH3CHO (g) + CCl2O (g)	Δ_rH°(0 K) = 9.60 ± 1.0 kcal/mol	Ruscic G4
2.5	5115.4	CH3C(O)OH (cr,l) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.326 ± 0.150 kcal/mol	Pickering 1895, Parker 1965, est unc
2.5	5115.5	CH3C(O)OH (cr,l) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.364 ± 0.150 kcal/mol	Thomsen 1882, Parker 1965, est unc
2.5	5115.7	CH3C(O)OH (cr,l) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.350 ± 0.150 kcal/mol	Berthelot 1875b, Parker 1965, est unc
2.5	5115.2	CH3C(O)OH (cr,l) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.361 ± 0.150 kcal/mol	Pritchard 1950, Parker 1965, est unc
2.5	5115.3	CH3C(O)OH (cr,l) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.347 ± 0.150 kcal/mol	Klibanova 1933, Parker 1965, est unc
2.3	5215.3	2 CH3C(O)Cl (g) + CH2O (g) → 2 CH3CHO (g) + CCl2O (g)	Δ_rH°(0 K) = 9.85 ± 1.1 kcal/mol	Ruscic G3X
2.0	5214.8	CH3C(O)Cl (g) → CH3CO (g) + Cl (g)	Δ_rH°(0 K) = 83.42 ± 0.6 kcal/mol	Tang 2008, est unc
1.8	5114.1	CH3C(O)OH (cr,l) + 2 O2 (g) → 2 CO2 (g) + 2 H2O (cr,l)	Δ_rH°(298.15 K) = -874.54 ± 0.30 (×1.414) kJ/mol	Evans 1959
1.7	5115.6	CH3C(O)OH (cr,l) → CH3C(O)OH (aq)	Δ_rH°(298.15 K) = -0.446 ± 0.180 kcal/mol	Carson 1949, Parker 1965, est unc
1.6	5215.6	2 CH3C(O)Cl (g) + CH2O (g) → 2 CH3CHO (g) + CCl2O (g)	Δ_rH°(0 K) = 10.01 ± 1.3 kcal/mol	Ruscic CBS-n
0.9	5220.2	CH3C(O)Cl (l) + H2O (cr,l) → CH3C(O)OH (aq, 1500 H2O) + HCl (aq, 1500 H2O)	Δ_rH°(298.15 K) = -22.55 ± 0.34 kcal/mol	Devore 1969

Top 10 species with enthalpies of formation correlated to the Δ_fH° of CH3C(O)Cl (l)

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
99.0	Acetyl chloride	CH3C(O)Cl (g)	-232.51	-241.50	± 0.39	kJ/mol	78.4973 ± 0.0019	75-36-5*0
76.1	Acetic acid	CH3C(O)OH (aq, 75 H2O)		-484.60	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*825
76.1	Acetic acid	CH3C(O)OH (aq, 100 H2O)		-484.65	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*828
76.1	Acetic acid	CH3C(O)OH (aq, 5000 H2O)		-484.69	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*844
76.1	Acetic acid	CH3C(O)OH (aq, 20000 H2O)		-484.84	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*852
76.1	Acetic acid	CH3C(O)OH (aq, 10000 H2O)		-484.83	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*850
76.1	Acetic acid	CH3C(O)OH (aq, 500 H2O)		-484.78	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*833
76.1	Acetic acid	CH3C(O)OH (aq, 7 H2O)		-483.35	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*812
76.1	Acetic acid	CH3C(O)OH (aq, 1000 H2O)		-484.80	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*839
76.1	Acetic acid	CH3C(O)OH (aq, 50000 H2O)		-484.85	± 0.33	kJ/mol	60.0520 ± 0.0017	64-19-7*855

Most Influential reactions involving CH3C(O)Cl (l)

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
0.926	5218.7	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rG°(298.15 K) = 2.416 ± 0.055 kJ/mol	McDonald 1959, 3rd Law
0.725	5219.1	CH3C(O)Cl (l) + H2O (cr,l) → CH3C(O)OH (aq, 75 H2O) + HCl (aq, 75 H2O)	Δ_rH°(298.15 K) = -22.07 ± 0.07 kcal/mol	Carson 1949
0.170	5220.1	CH3C(O)Cl (l) + H2O (cr,l) → CH3C(O)OH (aq, 1500 H2O) + HCl (aq, 1500 H2O)	Δ_rH°(298.15 K) = -22.22 ± 0.10 (×1.445) kcal/mol	Pritchard 1950, Parker 1965, NBS Tables 1989
0.030	5220.2	CH3C(O)Cl (l) + H2O (cr,l) → CH3C(O)OH (aq, 1500 H2O) + HCl (aq, 1500 H2O)	Δ_rH°(298.15 K) = -22.55 ± 0.34 kcal/mol	Devore 1969
0.017	5218.3	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rG°(298.15 K) = 2.19 ± 0.40 kJ/mol	NBS Tables 1989
0.017	5218.2	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rH°(298.15 K) = 30.29 ± 0.40 kJ/mol	NBS Tables 1989
0.013	5218.8	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rH°(298.15 K) = 31.02 ± 0.32 (×1.445) kJ/mol	McDonald 1959, 2nd Law
0.009	5218.1	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rH°(298.15 K) = 30.03 ± 0.24 (×2.229) kJ/mol	ThermoData 2004
0.007	5218.5	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rG°(298.15 K) = 0.43 ± 0.02 (×7.336) kcal/mol	Devore 1969, 3rd Law
0.005	5218.4	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rH°(298.15 K) = 7.13 ± 0.05 (×3.513) kcal/mol	Mathews 1931, est unc
0.000	5218.6	CH3C(O)Cl (l) → CH3C(O)Cl (g)	Δ_rH°(298.15 K) = 5.72 ± 0.07 (×23.12) kcal/mol	Devore 1969, 2nd Law

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. 1.202 of the Thermochemical Network (2024); available at ATcT.anl.gov
4		B. Ruscic and D. H. Bross Accurate and Reliable Thermochemistry by Data Analysis of Complex Thermochemical Networks using Active Thermochemical Tables: The Case of Glycine Thermochemistry Faraday Discuss. (in press) (2024) [DOI: 10.1039/D4FD00110A]
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.