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].

Bromobenzene

Formula: C6H5Br (g)

CAS RN: 108-86-1

ATcT ID: 108-86-1*0

SMILES: c1ccc(cc1)Br

SMILES: c1ccccc1Br

InChI: InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H

InChIKey: QARVLSVVCXYDNA-UHFFFAOYSA-N

Hills Formula: C6H5Br1

2D Image:

Aliases: Bromobenzene; Monobromobenzene; Phenyl bromide; C6H5Br; NSC 6529

Relative Molecular Mass: 157.0079 ± 0.0049

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
127.0	104.9	± 1.3	kJ/mol

3D Image of C6H5Br (g)

spin ON spin OFF

Top contributors to the provenance of Δ_fH° of C6H5Br (g)

The 20 contributors listed below account only for 83.4% of the provenance of Δ_fH° of C6H5Br (g).
A total of 35 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
15.1	7369.1	C6H5Br (cr,l) + HCl (g) → C6H6 (cr,l) + 1/2 Br2 (cr,l) + 1/2 Cl2 (g)	Δ_rH°(298.15 K) = 19.98 ± 0.78 kcal/mol	Chernick 1956, Hartley 1951
14.7	7382.1	C6H5I (cr,l) + 1/2 Br2 (cr,l) → C6H5Br (cr,l) + 1/2 I2 (cr,l)	Δ_rH°(298.15 K) = -12.85 ± 0.55 kcal/mol	Chernick 1956, Hartley 1951
10.1	7363.2	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.827 ± 0.030 eV	Stevens 2009
6.7	7363.1	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.781 ± 0.029 (×1.269) eV	Stevens 2009
6.6	7362.1	C6H5Cl (g) + Br (g) → C6H5Br (g) + Cl (g)	Δ_rH°(0 K) = 0.647 ± 0.049 eV	Stevens 2009
4.8	7363.5	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 273.5 ± 1 kcal/mol	Pratt 1981
3.6	7350.4	C6H5Br (g) → 6 C (g) + 5 H (g) + Br (g)	Δ_rH°(0 K) = 1276.98 ± 1.60 kcal/mol	Ruscic G4
3.3	7362.2	C6H5Cl (g) + Br (g) → C6H5Br (g) + Cl (g)	Δ_rH°(0 K) = 0.647 ± 0.069 eV	Stevens 2009
3.1	7350.3	C6H5Br (g) → 6 C (g) + 5 H (g) + Br (g)	Δ_rH°(0 K) = 1277.62 ± 1.72 kcal/mol	Ruscic G3X
2.5	7364.1	[C6H5Br]+ (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 2.76 ± 0.02 (×3.018) eV	Rosenstock 1980, Baer 1982
1.9	7363.7	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.75 ± 0.05 (×1.354) eV	Sergeev 1970
1.8	7364.2	[C6H5Br]+ (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 2.81 ± 0.07 eV	Dunbar 1984
1.5	7384.1	C6H5I (cr,l) + HCl (g) → C6H6 (cr,l) + 1/2 I2 (cr,l) + 1/2 Cl2 (g)	Δ_rH°(298.15 K) = 7.13 ± 0.75 kcal/mol	Chernick 1956, Hartley 1951
1.4	7364.3	[C6H5Br]+ (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 2.90 ± 0.05 (×1.61) eV	Lifshitz 1991, est unc
1.1	7363.6	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.73 ± 0.05 (×1.756) eV	Malinovich 1985
0.9	7393.1	C6H5NO (g) → [C6H5]+ (g) + NO (g)	Δ_rH°(0 K) = 10.607 ± 0.020 eV	Stevens 2010a
0.9	7364.4	[C6H5Br]+ (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 2.74 ± 0.10 eV	Dunbar 1985, Dunbar 1984, est unc
0.9	7381.1	2 C6H5I (cr,l) + 29/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) + I2 (cr,l)	Δ_rH°(298.15 K) = -1526.32 ± 2.0 kcal/mol	Smith 1956
0.8	6884.9	[C6H5]+ (g) → 6 C (g) + 5 H (g)	Δ_rH°(0 K) = 4198.8 ± 4 kJ/mol	Lau 2006
0.7	6882.14	C6H5 (g) → [C6H5]+ (g)	Δ_rH°(0 K) = 8.261 ± 0.035 eV	Lau 2006

Top 10 species with enthalpies of formation correlated to the Δ_fH° of C6H5Br (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
99.9	Bromobenzene cation	[C6H5Br]+ (g)	995.1	973.6	± 1.3	kJ/mol	157.0074 ± 0.0049	55450-33-4*0
99.1	Bromobenzene	C6H5Br (cr,l)		60.3	± 1.3	kJ/mol	157.0079 ± 0.0049	108-86-1*500
44.2	Phenylium	[C6H5]+ (g)	1149.28	1136.50	± 0.85	kJ/mol	77.1034 ± 0.0048	17333-73-2*0
44.2	Phenylium	[C6H5]+ (g, singlet)	1149.28	1136.50	± 0.85	kJ/mol	77.1034 ± 0.0048	17333-73-2*2
38.9	Iodobenzene	C6H5I (cr,l)	113.7	113.8	± 1.1	kJ/mol	204.0084 ± 0.0048	591-50-4*500
38.7	Iodobenzene	C6H5I (g)	178.59	162.60	± 0.99	kJ/mol	204.0084 ± 0.0048	591-50-4*0
38.6	Iodobenzene cation	[C6H5I]+ (g)	1023.59	1008.15	± 0.99	kJ/mol	204.0078 ± 0.0048	38406-85-8*0
16.6	Nitrosobenzene	C6H5NO (g)	216.9	199.9	± 1.2	kJ/mol	107.1100 ± 0.0048	586-96-9*0
16.5	Phenylium	[C6H5]+ (g, triplet)	1251.3	1238.2	± 1.6	kJ/mol	77.1034 ± 0.0048	17333-73-2*1
13.7	Phenyl	C6H5 (g)	352.61	339.25	± 0.60	kJ/mol	77.1039 ± 0.0048	2396-01-2*0

Most Influential reactions involving C6H5Br (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
0.979	7351.1	C6H5Br (g) → [C6H5Br]+ (g)	Δ_rH°(0 K) = 72570 ± 5 cm-1	Kwon 2002
0.587	7366.1	C6H5Br (cr,l) → C6H5Br (g)	Δ_rH°(298.15 K) = 44.54 ± 0.22 kJ/mol	Majer 1985, Wadso 1968
0.315	7366.3	C6H5Br (cr,l) → C6H5Br (g)	Δ_rH°(298.15 K) = 44.84 ± 0.30 kJ/mol	Basarova 1991, Boublik 1984
0.170	7363.2	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.827 ± 0.030 eV	Stevens 2009
0.113	7363.1	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.781 ± 0.029 (×1.269) eV	Stevens 2009
0.090	7366.2	C6H5Br (cr,l) → C6H5Br (g)	Δ_rH°(298.15 K) = 44.79 ± 0.56 kJ/mol	ThermoData 2004
0.083	7362.1	C6H5Cl (g) + Br (g) → C6H5Br (g) + Cl (g)	Δ_rH°(0 K) = 0.647 ± 0.049 eV	Stevens 2009
0.081	7363.5	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 273.5 ± 1 kcal/mol	Pratt 1981
0.041	7362.2	C6H5Cl (g) + Br (g) → C6H5Br (g) + Cl (g)	Δ_rH°(0 K) = 0.647 ± 0.069 eV	Stevens 2009
0.037	7350.4	C6H5Br (g) → 6 C (g) + 5 H (g) + Br (g)	Δ_rH°(0 K) = 1276.98 ± 1.60 kcal/mol	Ruscic G4
0.033	7363.7	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.75 ± 0.05 (×1.354) eV	Sergeev 1970
0.032	7350.3	C6H5Br (g) → 6 C (g) + 5 H (g) + Br (g)	Δ_rH°(0 K) = 1277.62 ± 1.72 kcal/mol	Ruscic G3X
0.019	7363.6	C6H5Br (g) → [C6H5]+ (g) + Br (g)	Δ_rH°(0 K) = 11.73 ± 0.05 (×1.756) eV	Malinovich 1985
0.009	7351.2	C6H5Br (g) → [C6H5Br]+ (g)	Δ_rH°(0 K) = 8.991 ± 0.002 (×3.221) eV	Holland 2000
0.004	7365.3	C6H5Br (g) → C6H5 (g) + Br (g)	Δ_rH°(1080 K) = 78.1 ± 5 kcal/mol	Rodgers 1967, Ladacki 1953, est unc
0.003	6920.1	C6H5Br (g) → C6H4 (g) + Br- (g) + H+ (g)	Δ_rH°(298.15 K) = 397 ± 6 kcal/mol	Wenthold 1994, note unc2
0.001	7390.1	C6H5Br (g) + [C6H5F]+ (g) → [C6H5Br]+ (g) + C6H5F (g)	Δ_rH°(350 K) = -4.95 ± 0.5 kcal/mol	Lias 1978, 2nd Law, est unc
0.000	7351.3	C6H5Br (g) → [C6H5Br]+ (g)	Δ_rH°(0 K) = 8.998 ± 0.02 eV	Potts 1980a, est unc, von Niessen 1982
0.000	7351.9	C6H5Br (g) → [C6H5Br]+ (g)	Δ_rH°(0 K) = 8.98 ± 0.02 eV	Watanabe 1957
0.000	7351.4	C6H5Br (g) → [C6H5Br]+ (g)	Δ_rH°(0 K) = 8.98 ± 0.02 eV	Walter 1991

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.