Selected ATcT [1, 2] enthalpy of formation based on version 1.130 of the Thermochemical Network [3]

This version of ATcT results[4] was generated by additional expansion of version 1.128 [5,6] to include with the calculations provided in reference [4].

Phenol

Formula: C6H5OH (g)

CAS RN: 108-95-2

ATcT ID: 108-95-2*0

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
-74.70	-93.30	± 0.63	kJ/mol

3D Image of C6H5OH (g)

spin ON spin OFF

Top contributors to the provenance of Δ_fH° of C6H5OH (g)

The 20 contributors listed below account only for 68.6% of the provenance of Δ_fH° of C6H5OH (g).
A total of 45 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
23.4	6694.2	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
5.5	6695.1	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.41 ± 0.12 kcal/mol	Andon 1960, Cox 1961a
3.5	6694.1	C6H5OH (cr,l) + 7 O2 (g) → 6 CO2 (g) + 3 H2O (cr,l)	Δ_rH°(298.15 K) = -729.78 ± 0.16 (×3.83) kcal/mol	Andon 1960, Cox 1961a
2.5	6691.5	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.05 ± 0.85 kcal/mol	Ruscic W1RO
2.5	6693.5	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 6.05 ± 0.85 kcal/mol	Ruscic W1RO
2.5	6694.3	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
2.3	6691.1	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.42 ± 0.90 kcal/mol	Ruscic G3X
2.3	6691.2	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.09 ± 0.90 kcal/mol	Ruscic G4
2.3	6691.4	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.69 ± 0.90 kcal/mol	Ruscic CBS-n
2.3	6693.2	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 5.50 ± 0.90 kcal/mol	Ruscic G4
2.3	6693.4	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 6.30 ± 0.90 kcal/mol	Ruscic CBS-n
2.3	6693.1	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 6.03 ± 0.90 kcal/mol	Ruscic G3X
2.2	6692.5	C6H5OH (g) + CH2CH2 (g) → CH2CHOH (g, syn) + C6H6 (g)	Δ_rH°(0 K) = -0.12 ± 0.9 kcal/mol	Ruscic W1RO
1.8	6691.3	C6H5OH (g) + CH3CH3 (g) → C6H6 (g) + CH3CH2OH (g)	Δ_rH°(0 K) = 6.23 ± 1.0 kcal/mol	Ruscic CBS-n
1.8	6693.3	C6H5OH (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3OH (g)	Δ_rH°(0 K) = 5.87 ± 1.0 kcal/mol	Ruscic CBS-n
1.8	6692.4	C6H5OH (g) + CH2CH2 (g) → CH2CHOH (g, syn) + C6H6 (g)	Δ_rH°(0 K) = 0.24 ± 1.0 kcal/mol	Ruscic CBS-n
1.8	6692.2	C6H5OH (g) + CH2CH2 (g) → CH2CHOH (g, syn) + C6H6 (g)	Δ_rH°(0 K) = 0.31 ± 1.0 kcal/mol	Ruscic G4
1.6	6710.5	C6H5OCH3 (g) + CH3OH (g) → C6H5OH (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -1.21 ± 0.9 kcal/mol	Ruscic W1RO
1.6	6695.2	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.65 ± 0.22 kcal/mol	Stohmann 1892, Parsons 1971
1.4	6692.1	C6H5OH (g) + CH2CH2 (g) → CH2CHOH (g, syn) + C6H6 (g)	Δ_rH°(0 K) = 0.57 ± 1.1 kcal/mol	Ruscic G3X

Top 10 species with enthalpies of formation correlated to the Δ_fH° of C6H5OH (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
98.5	Phenol cation	[C6H5OH]+ (g)	746.14	727.35	± 0.63	kJ/mol	94.1107 ± 0.0048	40932-22-7*0
78.6	Phenol	C6H5OH (cr,l)	-146.45	-162.30	± 0.65	kJ/mol	94.1112 ± 0.0048	108-95-2*500
65.3	Phenolate	[C6H5O]- (g)	-146.46	-161.93	± 0.84	kJ/mol	93.1038 ± 0.0048	3229-70-7*0
65.1	Phenoxy	C6H5O (g)	71.00	55.71	± 0.84	kJ/mol	93.1033 ± 0.0048	2122-46-5*0
32.1	Phenylperoxy	C6H5OO (g)	153.5	136.5	± 1.4	kJ/mol	109.1027 ± 0.0049	91422-02-5*0
21.3	Phenyl hydroperoxide	C6H5OOH (g)	13.3	-5.7	± 2.1	kJ/mol	110.1106 ± 0.0049	36112-26-2*0
18.8	Phenyloxoniumylidene	[C6H5O]+ (g)	901.5	887.1	± 2.2	kJ/mol	93.1028 ± 0.0048	41071-17-4*0
16.6	Benzene	C6H6 (g)	100.71	83.20	± 0.21	kJ/mol	78.1118 ± 0.0048	71-43-2*0
16.6	Benzene cation	[C6H6]+ (g)	992.61	976.14	± 0.21	kJ/mol	78.1113 ± 0.0048	34504-50-2*0
16.6	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 (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
1.000	6689.1	[C6H5OH]- (g) → C6H5OH (g)	Δ_rH°(0 K) = -1.01 ± 0.05 eV	Jordan 1976
0.676	6695.1	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.41 ± 0.12 kcal/mol	Andon 1960, Cox 1961a
0.348	6688.2	C6H5OH (g) → [C6H5OH]+ (g)	Δ_rH°(0 K) = 68621 ± 15 cm-1	Lemaire 1987, est unc
0.348	6688.1	C6H5OH (g) → [C6H5OH]+ (g)	Δ_rH°(0 K) = 68623 ± 15 cm-1	Lipert 1990, est unc
0.301	6688.3	C6H5OH (g) → [C6H5OH]+ (g)	Δ_rH°(0 K) = 8.506 ± 0.002 eV	Fuke 1984, note unc
0.201	6695.2	C6H5OH (cr,l) → C6H5OH (g)	Δ_rH°(298.15 K) = 16.65 ± 0.22 kcal/mol	Stohmann 1892, Parsons 1971
0.194	6706.1	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rG°(500 K) = -4.9 ± 0.4 kcal/mol	Cumming 1978
0.091	6705.2	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rG°(500 K) = -13.2 ± 0.5 kcal/mol	Cumming 1978
0.068	4950.5	[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
0.066	6710.5	C6H5OCH3 (g) + CH3OH (g) → C6H5OH (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -1.21 ± 0.9 kcal/mol	Ruscic W1RO
0.055	6701.1	C6H5OH (g) → C6H5O (g) + H (g)	Δ_rH°(0 K) = 30015 ± 40 (×5.657) cm-1	Nix 2006
0.053	6710.4	C6H5OCH3 (g) + CH3OH (g) → C6H5OH (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -0.94 ± 1.0 kcal/mol	Ruscic CBS-n
0.053	6710.2	C6H5OCH3 (g) + CH3OH (g) → C6H5OH (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -0.91 ± 1.0 kcal/mol	Ruscic G4
0.048	6706.6	[C6H5O]- (g) + HC(O)OH (g) → C6H5OH (g) + [HC(O)O]- (g)	Δ_rH°(0 K) = -5.30 ± 0.8 kcal/mol	Ruscic W1RO
0.044	6710.1	C6H5OCH3 (g) + CH3OH (g) → C6H5OH (g) + CH3OCH3 (g)	Δ_rH°(0 K) = -0.84 ± 1.1 kcal/mol	Ruscic G3X
0.043	4950.4	[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
0.043	4950.2	[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
0.038	6704.6	[C6H5O]- (g) + HOO (g) → C6H5OH (g) + [O2]- (g)	Δ_rH°(0 K) = 0.148 ± 0.035 eV	Ruscic W1RO
0.035	6705.5	[C6H5O]- (g) + HCl (g) → C6H5OH (g) + Cl- (g)	Δ_rH°(0 K) = -16.04 ± 0.8 kcal/mol	Ruscic W1RO
0.035	6703.7	[C6H5O]- (g) + HCN (g) → C6H5OH (g) + [CN]- (g)	Δ_rH°(0 K) = 0.052 ± 0.035 eV	Ruscic W1RO

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. 1.130 of the Thermochemical Network. Argonne National Laboratory, Lemont, Illinois 2023; available at ATcT.anl.gov [DOI: 10.17038/CSE/1997229]
4		N. Genossar, P. B. Changala, B. Gans, J.-C. Loison, S. Hartweg, M.-A. Martin-Drumel, G. A. Garcia, J. F. Stanton, B. Ruscic, and J. H. Baraban Ring-Opening Dynamics of the Cyclopropyl Radical and Cation: the Transition State Nature of the Cyclopropyl Cation J. Am. Chem. Soc. 144, 18518-18525 (2022) [DOI: 10.1021/jacs.2c07740]
5		B. Ruscic and D. H. Bross Active Thermochemical Tables: The Thermophysical and Thermochemical Properties of Methyl, CH3, and Methylene, CH2, Corrected for Nonrigid Rotor and Anharmonic Oscillator Effects. Mol. Phys. e1969046 (2021) [DOI: 10.1080/00268976.2021.1969046]
6		J. H. Thorpe, J. L. Kilburn, D. Feller, P. B. Changala, D. H. Bross, B. Ruscic, and J. F. Stanton, Elaborated Thermochemical Treatment of HF, CO, N2, and H2O: Insight into HEAT and Its Extensions J. Chem. Phys. 155, 184109 (2021) [DOI: 10.1063/5.0069322]
7		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]
8		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]).
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.