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].

Phenoxy

Formula: C6H5O (g)

CAS RN: 2122-46-5

ATcT ID: 2122-46-5*0

SMILES: c1ccc(cc1)[O]

InChI: InChI=1S/C6H5O/c7-6-4-2-1-3-5-6/h1-5H

InChIKey: KHUXNRRPPZOJPT-UHFFFAOYSA-N

Hills Formula: C6H5O1

2D Image:

Aliases: C6H5O; Phenoxy; Phenyloxidanyl; Phenoxy radical; Phenoxyl; Phenoxyl radical; Phenyloxy; Phenoxide radical

Relative Molecular Mass: 93.1033 ± 0.0048

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
71.38	56.09	± 0.83	kJ/mol

3D Image of C6H5O (g)

spin ON spin OFF

Top contributors to the provenance of Δ_fH° of C6H5O (g)

The 20 contributors listed below account only for 45.0% of the provenance of Δ_fH° of C6H5O (g).
A total of 90 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
9.8	7023.2	C6H5OH (cr,l) + 7 O2 (g) → 6 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -730.38 ± 0.24 kcal/mol	Parks 1954
4.1	7035.1	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rG°(500 K) = -4.9 ± 0.4 kcal/mol	Cumming 1978
4.0	7034.2	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rG°(500 K) = -13.2 ± 0.5 kcal/mol	Cumming 1978
2.3	7030.1	C6H5OH (g) → C6H5O (g) + H (g)	Δ_rH°(0 K) = 30015 ± 40 (×5.781) cm-1	Nix 2006
2.2	7024.1	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.41 ± 0.12 kcal/mol	Andon 1960, Cox 1961a
1.9	8246.2	C6H5OO (g) + CH3 (g) → C6H5 (g) + CH3OO (g)	Δ_rH°(0 K) = 16.66 ± 1.0 kcal/mol	Ruscic G4
1.6	7025.5	C6H5O (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1320.77 ± 1.50 kcal/mol	Ruscic W1RO
1.6	8246.1	C6H5OO (g) + CH3 (g) → C6H5 (g) + CH3OO (g)	Δ_rH°(0 K) = 17.83 ± 1.1 kcal/mol	Ruscic G3X
1.6	7029.6	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1371.16 ± 1.5 kcal/mol	Gutowski 2006, est unc
1.6	7029.5	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1373.33 ± 1.50 kcal/mol	Ruscic W1RO
1.5	7034.5	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rH°(0 K) = -16.04 ± 0.8 kcal/mol	Ruscic W1RO
1.5	7032.7	[C6H5O]- (g) + HCN (g) → C6H5OH (g) + [CN]- (g)	Δ_rH°(0 K) = 0.052 ± 0.035 eV	Ruscic W1RO
1.5	7033.6	[C6H5O]- (g) + HOO (g) → C6H5OH (g) + [O2]- (g)	Δ_rH°(0 K) = 0.148 ± 0.035 eV	Ruscic W1RO
1.4	7025.2	C6H5O (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1319.66 ± 1.60 kcal/mol	Ruscic G4
1.4	7029.2	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1372.84 ± 1.60 kcal/mol	Ruscic G4
1.3	7028.5	[C6H5O]+ (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1122.42 ± 1.50 kcal/mol	Ruscic W1RO
1.2	7025.1	C6H5O (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1318.87 ± 1.72 kcal/mol	Ruscic G3X
1.2	7031.5	C6H5OH (g) → [C6H5O]- (g) + H+ (g)	Δ_rH°(0 K) = 348.53 ± 0.90 kcal/mol	Ruscic W1RO
1.2	7029.1	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1372.80 ± 1.72 kcal/mol	Ruscic G3X
1.2	7023.1	C6H5OH (cr,l) + 7 O2 (g) → 6 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -729.78 ± 0.16 (×4.269) kcal/mol	Andon 1960, Cox 1961a

Top 10 species with enthalpies of formation correlated to the Δ_fH° of C6H5O (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
99.5	Phenolate	[C6H5O]- (g)	-146.08	-161.55	± 0.83	kJ/mol	93.1038 ± 0.0048	3229-70-7*0
65.0	Phenol	C6H5OH (g)	-74.39	-92.98	± 0.63	kJ/mol	94.1112 ± 0.0048	108-95-2*0
64.1	Phenol cation	[C6H5OH]+ (g)	746.45	727.66	± 0.63	kJ/mol	94.1107 ± 0.0048	40932-22-7*0
54.2	Phenyloxoniumylidene	[C6H5O]+ (g)	898.6	884.2	± 1.4	kJ/mol	93.1028 ± 0.0048	41071-17-4*0
51.2	Phenol	C6H5OH (cr,l)	-146.19	-162.04	± 0.65	kJ/mol	94.1112 ± 0.0048	108-95-2*500
48.9	Phenylperoxy	C6H5OO (g)	153.8	136.8	± 1.4	kJ/mol	109.1027 ± 0.0049	91422-02-5*0
32.3	Phenyl hydroperoxide	C6H5OOH (g)	13.7	-5.4	± 2.1	kJ/mol	110.1106 ± 0.0049	36112-26-2*0
21.2	Phenylperoxy cation	[C6H5OO]+ (g)	1018.9	1001.9	± 3.1	kJ/mol	109.1022 ± 0.0049	956036-17-2*0
20.0	Phenylperoxy anion	[C6H5OO]- (g)	-38.9	-55.9	± 3.3	kJ/mol	109.1032 ± 0.0049	956036-17-20
14.4	Formate	[HC(O)O]- (g)	-463.13	-466.77	± 0.55	kJ/mol	45.0180 ± 0.0010	71-47-6*0

Most Influential reactions involving C6H5O (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
0.975	7027.1	[C6H5O]- (g) → C6H5O (g)	Δ_rH°(0 K) = 18178 ± 7 cm-1	Kim 2011
0.375	7026.1	C6H5O (g) → [C6H5O]+ (g)	Δ_rH°(0 K) = 8.56 ± 0.02 eV	Fernholz 2022, est unc
0.375	7026.2	C6H5O (g) → [C6H5O]+ (g)	Δ_rH°(0 K) = 8.56 ± 0.02 eV	Dewar 1980
0.098	8244.5	C6H5OO (g) + CH3O (g) → C6H5O (g) + CH3OO (g)	Δ_rH°(0 K) = -21.48 ± 0.9 kcal/mol	Ruscic W1RO
0.098	8245.5	C6H5OO (g) + OH (g) → C6H5O (g) + HOO (g)	Δ_rH°(0 K) = -25.75 ± 0.9 kcal/mol	Ruscic W1RO
0.093	7026.7	C6H5O (g) → [C6H5O]+ (g)	Δ_rH°(0 K) = 8.601 ± 0.040 eV	Ruscic W1RO
0.080	8244.2	C6H5OO (g) + CH3O (g) → C6H5O (g) + CH3OO (g)	Δ_rH°(0 K) = -20.35 ± 1.0 kcal/mol	Ruscic G4
0.080	8244.4	C6H5OO (g) + CH3O (g) → C6H5O (g) + CH3OO (g)	Δ_rH°(0 K) = -21.73 ± 1.0 kcal/mol	Ruscic CBS-n
0.079	8245.4	C6H5OO (g) + OH (g) → C6H5O (g) + HOO (g)	Δ_rH°(0 K) = -25.34 ± 1.0 kcal/mol	Ruscic CBS-n
0.073	8245.2	C6H5OO (g) + OH (g) → C6H5O (g) + HOO (g)	Δ_rH°(0 K) = -23.97 ± 1.0 (×1.044) kcal/mol	Ruscic G4
0.066	8244.1	C6H5OO (g) + CH3O (g) → C6H5O (g) + CH3OO (g)	Δ_rH°(0 K) = -20.72 ± 1.1 kcal/mol	Ruscic G3X
0.065	8245.1	C6H5OO (g) + OH (g) → C6H5O (g) + HOO (g)	Δ_rH°(0 K) = -24.13 ± 1.1 kcal/mol	Ruscic G3X
0.052	7030.1	C6H5OH (g) → C6H5O (g) + H (g)	Δ_rH°(0 K) = 30015 ± 40 (×5.781) cm-1	Nix 2006
0.035	8243.5	C6H5OO (g) → C6H5O (g) + O (g)	Δ_rH°(0 K) = 38.19 ± 1.50 kcal/mol	Ruscic W1RO
0.031	8243.2	C6H5OO (g) → C6H5O (g) + O (g)	Δ_rH°(0 K) = 39.84 ± 1.60 kcal/mol	Ruscic G4
0.031	8243.4	C6H5OO (g) → C6H5O (g) + O (g)	Δ_rH°(0 K) = 39.29 ± 1.60 kcal/mol	Ruscic CBS-n
0.029	7036.6	C6H5O (g) + CH3CH2CH2CH2 (g) → C6H5OH (g) + CH2CHCH2CH3 (g)	Δ_rH°(0 K) = -54.93 ± 1.2 kcal/mol	Ruscic W1RO
0.028	7026.4	C6H5O (g) → [C6H5O]+ (g)	Δ_rH°(0 K) = 8.626 ± 0.073 eV	Ruscic G4
0.026	8243.1	C6H5OO (g) → C6H5O (g) + O (g)	Δ_rH°(0 K) = 39.27 ± 1.72 kcal/mol	Ruscic G3X
0.025	7036.3	C6H5O (g) + CH3CH2CH2CH2 (g) → C6H5OH (g) + CH2CHCH2CH3 (g)	Δ_rH°(0 K) = -53.44 ± 1.3 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. 1.156 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.