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].

Phenolate

Formula: [C6H5O]- (g)

CAS RN: 3229-70-7

ATcT ID: 3229-70-7*0

SMILES: c1ccc(cc1)[O-]

InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H/p-1

InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-M

SMILES: C1=C[CH-]C(=O)C=C1

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

InChIKey: FABJBXYZKYBFAM-UHFFFAOYSA-N

Hills Formula: C6H5O1-

2D Image:

Aliases: Phenolate; Phenate; Deprotonated phenol; Phenolate anion; Phenolate ion; Phenolate ion (1-); Phenoxide; Phenoxide anion; Phenoxide ion; [C6H5O]-; C6H5O-; 537047-71-5

Relative Molecular Mass: 93.1038 ± 0.0048

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
-145.95	-161.42	± 0.81	kJ/mol

3D Image of [C6H5O]- (g)

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

The 20 contributors listed below account only for 42.7% of the provenance of Δ_fH° of [C6H5O]- (g).
A total of 94 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
9.4	7172.2	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
3.9	7184.1	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rG°(500 K) = -4.9 ± 0.4 kcal/mol	Cumming 1978
3.8	7183.2	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rG°(500 K) = -13.2 ± 0.5 kcal/mol	Cumming 1978
2.1	7173.1	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.41 ± 0.12 kcal/mol	Andon 1960, Cox 1961a
1.9	7179.1	C6H5OH (g) → C6H5O (g) + H (g)	Δ_rH°(0 K) = 30015 ± 40 (×6.037) cm-1	Nix 2006
1.8	8437.2	C6H5OO (g) + CH3 (g) → C6H5 (g) + CH3OO (g)	Δ_rH°(0 K) = 16.66 ± 1.0 kcal/mol	Ruscic G4
1.5	7178.6	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1371.16 ± 1.5 kcal/mol	Gutowski 2006, est unc
1.5	7178.5	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1373.33 ± 1.50 kcal/mol	Ruscic W1RO
1.5	7174.5	C6H5O (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1320.77 ± 1.50 kcal/mol	Ruscic W1RO
1.5	8437.1	C6H5OO (g) + CH3 (g) → C6H5 (g) + CH3OO (g)	Δ_rH°(0 K) = 17.83 ± 1.1 kcal/mol	Ruscic G3X
1.5	7183.5	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rH°(0 K) = -16.04 ± 0.8 kcal/mol	Ruscic W1RO
1.4	7181.7	[C6H5O]- (g) + HCN (g) → C6H5OH (g) + [CN]- (g)	Δ_rH°(0 K) = 0.052 ± 0.035 eV	Ruscic W1RO
1.4	7182.6	[C6H5O]- (g) + HOO (g) → C6H5OH (g) + [O2]- (g)	Δ_rH°(0 K) = 0.148 ± 0.035 eV	Ruscic W1RO
1.3	7178.2	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1372.84 ± 1.60 kcal/mol	Ruscic G4
1.3	7174.2	C6H5O (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1319.66 ± 1.60 kcal/mol	Ruscic G4
1.3	7204.5	C6H5OCH3 (g) → C6H5O (g) + CH3 (g)	Δ_rH°(0 K) = 64.35 ± 1.50 kcal/mol	Ruscic W1RO
1.2	7177.5	[C6H5O]+ (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1122.42 ± 1.50 kcal/mol	Ruscic W1RO
1.1	7180.5	C6H5OH (g) → [C6H5O]- (g) + H+ (g)	Δ_rH°(0 K) = 348.53 ± 0.90 kcal/mol	Ruscic W1RO
1.1	7178.1	[C6H5O]- (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1372.80 ± 1.72 kcal/mol	Ruscic G3X
1.1	7174.1	C6H5O (g) → 6 C (g) + 5 H (g) + O (g)	Δ_rH°(0 K) = 1318.87 ± 1.72 kcal/mol	Ruscic G3X

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
99.4	Phenoxy	C6H5O (g)	71.51	56.22	± 0.81	kJ/mol	93.1033 ± 0.0048	2122-46-5*0
64.2	Phenol	C6H5OH (g)	-74.35	-92.94	± 0.62	kJ/mol	94.1112 ± 0.0048	108-95-2*0
63.3	Phenol cation	[C6H5OH]+ (g)	746.50	727.70	± 0.63	kJ/mol	94.1107 ± 0.0048	40932-22-7*0
52.8	Phenyloxoniumylidene	[C6H5O]+ (g)	898.7	884.4	± 1.4	kJ/mol	93.1028 ± 0.0048	41071-17-4*0
50.4	Phenol	C6H5OH (cr,l)	-146.16	-162.00	± 0.64	kJ/mol	94.1112 ± 0.0048	108-95-2*500
47.6	Phenylperoxy	C6H5OO (g)	153.9	136.9	± 1.4	kJ/mol	109.1027 ± 0.0049	91422-02-5*0
31.4	Phenyl hydroperoxide	C6H5OOH (g)	13.8	-5.2	± 2.1	kJ/mol	110.1106 ± 0.0049	36112-26-2*0
20.5	Phenylperoxy cation	[C6H5OO]+ (g)	1019.0	1002.0	± 3.1	kJ/mol	109.1022 ± 0.0049	956036-17-2*0
19.4	Phenylperoxy anion	[C6H5OO]- (g)	-38.8	-55.8	± 3.3	kJ/mol	109.1032 ± 0.0049	956036-17-20
14.0	Formate	[HC(O)O]- (g)	-463.10	-466.75	± 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	7176.1	[C6H5O]- (g) → C6H5O (g)	Δ_rH°(0 K) = 18178 ± 7 cm-1	Kim 2011
0.191	7184.1	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rG°(500 K) = -4.9 ± 0.4 kcal/mol	Cumming 1978
0.089	7183.2	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rG°(500 K) = -13.2 ± 0.5 kcal/mol	Cumming 1978
0.067	5293.5	[CH3C(O)O]- (g) + C6H5OH (g) → CH3C(O)OH (g, syn) + [C6H5O]- (g)	Δ_rH°(0 K) = 1.57 ± 0.8 kcal/mol	Ruscic W1RO
0.047	7184.6	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rH°(0 K) = -5.30 ± 0.8 kcal/mol	Ruscic W1RO
0.043	5293.2	[CH3C(O)O]- (g) + C6H5OH (g) → CH3C(O)OH (g, syn) + [C6H5O]- (g)	Δ_rH°(0 K) = 1.56 ± 1.0 kcal/mol	Ruscic G4
0.043	5293.4	[CH3C(O)O]- (g) + C6H5OH (g) → CH3C(O)OH (g, syn) + [C6H5O]- (g)	Δ_rH°(0 K) = 1.52 ± 1.0 kcal/mol	Ruscic CBS-n
0.037	7182.6	[C6H5O]- (g) + HOO (g) → C6H5OH (g) + [O2]- (g)	Δ_rH°(0 K) = 0.148 ± 0.035 eV	Ruscic W1RO
0.035	7183.5	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rH°(0 K) = -16.04 ± 0.8 kcal/mol	Ruscic W1RO
0.034	7181.7	[C6H5O]- (g) + HCN (g) → C6H5OH (g) + [CN]- (g)	Δ_rH°(0 K) = 0.052 ± 0.035 eV	Ruscic W1RO
0.030	7184.5	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rH°(0 K) = -5.06 ± 1.0 kcal/mol	Ruscic CBS-n
0.030	7184.3	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rH°(0 K) = -5.33 ± 1.0 kcal/mol	Ruscic G4
0.030	5293.1	[CH3C(O)O]- (g) + C6H5OH (g) → CH3C(O)OH (g, syn) + [C6H5O]- (g)	Δ_rH°(0 K) = 1.31 ± 1.2 kcal/mol	Ruscic G3X
0.027	7180.5	C6H5OH (g) → [C6H5O]- (g) + H+ (g)	Δ_rH°(0 K) = 348.53 ± 0.90 kcal/mol	Ruscic W1RO
0.025	5293.3	[CH3C(O)O]- (g) + C6H5OH (g) → CH3C(O)OH (g, syn) + [C6H5O]- (g)	Δ_rH°(0 K) = 2.07 ± 1.3 kcal/mol	Ruscic CBS-n
0.024	7182.5	[C6H5O]- (g) + HOO (g) → C6H5OH (g) + [O2]- (g)	Δ_rH°(0 K) = 0.172 ± 0.043 eV	Ruscic CBS-n
0.022	7181.4	[C6H5O]- (g) + HCN (g) → C6H5OH (g) + [CN]- (g)	Δ_rH°(0 K) = 0.068 ± 0.043 eV	Ruscic G4
0.022	7181.6	[C6H5O]- (g) + HCN (g) → C6H5OH (g) + [CN]- (g)	Δ_rH°(0 K) = 0.064 ± 0.043 eV	Ruscic CBS-n
0.021	7184.2	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rH°(0 K) = -5.07 ± 1.2 kcal/mol	Ruscic G3X
0.020	7176.2	[C6H5O]- (g) → C6H5O (g)	Δ_rH°(0 K) = 2.253 ± 0.006 eV	Gunion 1992

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.