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].

Phenol

Formula: C6H5OH (cr,l)

CAS RN: 108-95-2

ATcT ID: 108-95-2*500

SMILES: c1ccc(cc1)O

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

InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N

Hills Formula: C6H6O1

2D Image:

Aliases: C6H5OH; Phenol; Benzenol; Carbolic acid; Hydroxybenzene; Monohydroxybenzene; Monophenol; Oxybenzene; Phenic acid; Phenyl alcohol; Phenyl hydrate; Phenyl hydroxide; Phenylic acid; Phenylic alcohol; ENT 1814; NSC 36808

Relative Molecular Mass: 94.1112 ± 0.0048

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
-146.19	-162.04	± 0.65	kJ/mol

Top contributors to the provenance of Δ_fH° of C6H5OH (cr,l)

The 20 contributors listed below account only for 79.5% of the provenance of Δ_fH° of C6H5OH (cr,l).
A total of 37 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
38.7	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
9.3	7024.1	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.41 ± 0.12 kcal/mol	Andon 1960, Cox 1961a
4.7	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
4.1	7023.3	C6H5OH (cr,l) + 7 O2 (g) → 6 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -729.90 ± 0.73 kcal/mol	Badoche 1941, as quoted by Cox 1970
2.7	7024.2	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.65 ± 0.22 kcal/mol	Stohmann 1892, Parsons 1971
1.5	7022.5	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 6.05 ± 0.85 kcal/mol	Ruscic W1RO
1.5	7020.5	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.05 ± 0.85 kcal/mol	Ruscic W1RO
1.4	7022.1	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 6.03 ± 0.90 kcal/mol	Ruscic G3X
1.4	7022.2	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 5.50 ± 0.90 kcal/mol	Ruscic G4
1.4	7022.4	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 6.30 ± 0.90 kcal/mol	Ruscic CBS-n
1.4	7020.2	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.09 ± 0.90 kcal/mol	Ruscic G4
1.4	7020.4	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.69 ± 0.90 kcal/mol	Ruscic CBS-n
1.4	7020.1	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.42 ± 0.90 kcal/mol	Ruscic G3X
1.3	7021.5	C6H5OH (g) + CH2CH2 (g) → CH2CHOH (g, syn) + C6H6 (g)	Δ_rH°(0 K) = -0.12 ± 0.9 kcal/mol	Ruscic W1RO
1.1	7039.5	C6H5OCH3 (g) + CH3OH (g) → C6H5OH (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -1.21 ± 0.9 kcal/mol	Ruscic W1RO
1.1	7022.3	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 5.87 ± 1.0 kcal/mol	Ruscic CBS-n
1.1	7020.3	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.23 ± 1.0 kcal/mol	Ruscic CBS-n
1.1	7021.2	C6H5OH (g) + CH2CH2 (g) → CH2CHOH (g, syn) + C6H6 (g)	Δ_rH°(0 K) = 0.31 ± 1.0 kcal/mol	Ruscic G4
1.1	7021.4	C6H5OH (g) + CH2CH2 (g) → CH2CHOH (g, syn) + C6H6 (g)	Δ_rH°(0 K) = 0.24 ± 1.0 kcal/mol	Ruscic CBS-n
0.9	7039.4	C6H5OCH3 (g) + CH3OH (g) → C6H5OH (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -0.94 ± 1.0 kcal/mol	Ruscic CBS-n

Top 10 species with enthalpies of formation correlated to the Δ_fH° of C6H5OH (cr,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
78.6	Phenol	C6H5OH (g)	-74.39	-92.98	± 0.63	kJ/mol	94.1112 ± 0.0048	108-95-2*0
77.5	Phenol cation	[C6H5OH]+ (g)	746.45	727.66	± 0.63	kJ/mol	94.1107 ± 0.0048	40932-22-7*0
51.3	Phenolate	[C6H5O]- (g)	-146.08	-161.55	± 0.83	kJ/mol	93.1038 ± 0.0048	3229-70-7*0
51.2	Phenoxy	C6H5O (g)	71.38	56.09	± 0.83	kJ/mol	93.1033 ± 0.0048	2122-46-5*0
27.8	Phenyloxoniumylidene	[C6H5O]+ (g)	898.6	884.2	± 1.4	kJ/mol	93.1028 ± 0.0048	41071-17-4*0
25.3	Phenylperoxy	C6H5OO (g)	153.8	136.8	± 1.4	kJ/mol	109.1027 ± 0.0049	91422-02-5*0
16.7	Phenyl hydroperoxide	C6H5OOH (g)	13.7	-5.4	± 2.1	kJ/mol	110.1106 ± 0.0049	36112-26-2*0
14.5	Benzene	C6H6 (g)	100.71	83.20	± 0.21	kJ/mol	78.1118 ± 0.0048	71-43-2*0
14.5	Benzene cation	[C6H6]+ (g)	992.61	976.14	± 0.21	kJ/mol	78.1113 ± 0.0048	34504-50-2*0
14.5	Benzene	C6H6 (cr,l)	50.81	49.26	± 0.21	kJ/mol	78.1118 ± 0.0048	71-43-2*500

Most Influential reactions involving C6H5OH (cr,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
0.677	7024.1	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.41 ± 0.12 kcal/mol	Andon 1960, Cox 1961a
0.398	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
0.201	7024.2	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.65 ± 0.22 kcal/mol	Stohmann 1892, Parsons 1971
0.049	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
0.043	7023.3	C6H5OH (cr,l) + 7 O2 (g) → 6 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -729.90 ± 0.73 kcal/mol	Badoche 1941, as quoted by Cox 1970
0.001	7023.4	C6H5OH (cr,l) + 7 O2 (g) → 6 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -733.89 ± 2 (×1.719) kcal/mol	Hirsbrunner 1934, Barker 1925, Stohmann 1892, Parsons 1971, est unc

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.