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].

Nitrobenzene

Formula: C6H5N(O)O (cr,l)

CAS RN: 98-95-3

ATcT ID: 98-95-3*500

SMILES: c1ccc(cc1)[N+](=O)[O-]

InChI: InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H

InChIKey: LQNUZADURLCDLV-UHFFFAOYSA-N

Hills Formula: C6H5N1O2

2D Image:

Aliases: C6H5N(O)O; Nitrobenzene; Essence of Mirbane; Essence of Myrbane; Mirbane oil; Nitrobenzol; Oil of Mirbane; Oil of Myrbane; UN 1662; NSC 9573

Relative Molecular Mass: 123.1094 ± 0.0049

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
	7.3	± 1.3	kJ/mol

Top contributors to the provenance of Δ_fH° of C6H5N(O)O (cr,l)

The 14 contributors listed below account for 91.7% of the provenance of Δ_fH° of C6H5N(O)O (cr,l).

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
21.3	7398.2	2 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -6170.83 ± 3.8 (×1.477) kJ/mol	Verevkin 2014
10.2	7397.5	C6H5N(O)O (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3N(O)O (g)	Δ_rH°(0 K) = -0.15 ± 0.9 kcal/mol	Ruscic W1RO
8.2	7397.4	C6H5N(O)O (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3N(O)O (g)	Δ_rH°(0 K) = 0.20 ± 1.0 kcal/mol	Ruscic CBS-n
8.2	7397.2	C6H5N(O)O (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3N(O)O (g)	Δ_rH°(0 K) = -0.43 ± 1.0 kcal/mol	Ruscic G4
6.8	7397.1	C6H5N(O)O (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3N(O)O (g)	Δ_rH°(0 K) = 0.08 ± 1.1 kcal/mol	Ruscic G3X
5.7	7396.5	C6H5N(O)O (g) + NO (g) → C6H5NO (g) + ONO (g)	Δ_rH°(0 K) = 19.87 ± 0.9 kcal/mol	Ruscic W1RO
5.5	7398.1	2 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1476.136 ± 1.43 (×1.834) kcal/mol	Lebedeva 1971, Verevkin 2014
4.8	7397.3	C6H5N(O)O (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3N(O)O (g)	Δ_rH°(0 K) = 0.49 ± 1.3 kcal/mol	Ruscic CBS-n
4.6	7396.4	C6H5N(O)O (g) + NO (g) → C6H5NO (g) + ONO (g)	Δ_rH°(0 K) = 18.62 ± 1.0 kcal/mol	Ruscic CBS-n
4.6	7396.2	C6H5N(O)O (g) + NO (g) → C6H5NO (g) + ONO (g)	Δ_rH°(0 K) = 19.30 ± 1.0 kcal/mol	Ruscic G4
3.8	7396.1	C6H5N(O)O (g) + NO (g) → C6H5NO (g) + ONO (g)	Δ_rH°(0 K) = 19.75 ± 1.1 kcal/mol	Ruscic G3X
2.7	7396.3	C6H5N(O)O (g) + NO (g) → C6H5NO (g) + ONO (g)	Δ_rH°(0 K) = 20.28 ± 1.3 kcal/mol	Ruscic CBS-n
2.5	7394.1	C6H5NO (g) → C6H5 (g) + NO (g)	Δ_rG°(391 K) = 39.48 ± 0.5 kcal/mol	Park 1997, Yu 1994a, 3rd Law
2.1	7393.1	C6H5NO (g) → [C6H5]+ (g) + NO (g)	Δ_rH°(0 K) = 10.607 ± 0.020 eV	Stevens 2010a

Top 10 species with enthalpies of formation correlated to the Δ_fH° of C6H5N(O)O (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
99.7	Nitrobenzene	C6H5N(O)O (g)	82.3	62.3	± 1.3	kJ/mol	123.1094 ± 0.0049	98-95-3*0
34.7	Nitrosobenzene	C6H5NO (g)	216.9	199.9	± 1.2	kJ/mol	107.1100 ± 0.0048	586-96-9*0
14.2	Nitromethane	CH3N(O)O (g)	-60.75	-74.65	± 0.42	kJ/mol	61.0401 ± 0.0010	75-52-5*0
13.2	Phenylium	[C6H5]+ (g)	1149.28	1136.50	± 0.85	kJ/mol	77.1034 ± 0.0048	17333-73-2*0
13.2	Phenylium	[C6H5]+ (g, singlet)	1149.28	1136.50	± 0.85	kJ/mol	77.1034 ± 0.0048	17333-73-2*2
12.8	Nitromethane	CH3N(O)O (cr,l)	-114.10	-112.92	± 0.40	kJ/mol	61.0401 ± 0.0010	75-52-5*500
11.4	Toluene	C6H5CH3 (g)	73.35	50.06	± 0.31	kJ/mol	92.1384 ± 0.0056	108-88-3*0
11.3	Toluene	C6H5CH3 (l)	19.78	12.03	± 0.31	kJ/mol	92.1384 ± 0.0056	108-88-3*500
9.8	Phenyl	C6H5 (g)	352.61	339.25	± 0.60	kJ/mol	77.1039 ± 0.0048	2396-01-2*0
9.0	Iodobenzene	C6H5I (g)	178.59	162.60	± 0.99	kJ/mol	204.0084 ± 0.0048	591-50-4*0

Most Influential reactions involving C6H5N(O)O (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
0.946	7399.2	C6H5N(O)O (cr,l) → C6H5N(O)O (g)	Δ_rH°(298.15 K) = 55.013 ± 0.1 kJ/mol	Kusano 1971, Verevkin 2014
0.214	7398.2	2 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -6170.83 ± 3.8 (×1.477) kJ/mol	Verevkin 2014
0.056	7398.1	2 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1476.136 ± 1.43 (×1.834) kcal/mol	Lebedeva 1971, Verevkin 2014
0.037	7399.4	C6H5N(O)O (cr,l) → C6H5N(O)O (g)	Δ_rH°(298.15 K) = 55.3 ± 0.5 kJ/mol	Emmenegger 1999, est unc
0.005	7399.3	C6H5N(O)O (cr,l) → C6H5N(O)O (g)	Δ_rH°(298.15 K) = 56.32 ± 0.5 (×2.594) kJ/mol	Chickos 1995, est unc
0.005	7399.5	C6H5N(O)O (cr,l) → C6H5N(O)O (g)	Δ_rH°(298.15 K) = 55.0 ± 1.3 kJ/mol	Verevkin 2014, WinTable 2003
0.003	7399.1	C6H5N(O)O (cr,l) → C6H5N(O)O (g)	Δ_rH°(298.15 K) = 13.40 ± 0.40 kcal/mol	Lebedeva 1971, as quoted by Pedley 1986

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.