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:

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

   ΔfH°(0 K)   ΔfH°(298.15 K)UncertaintyUnits
7.3± 1.3kJ/mol

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

The 14 contributors listed below account for 91.7% of the provenance of ΔfH° 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
21.37398.2 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) N2 (g) ΔrH°(298.15 K) = -6170.83 ± 3.8 (×1.477) kJ/molVerevkin 2014
10.27397.5 C6H5N(O)O (g) CH3CH3 (g) → C6H5CH3 (g) CH3N(O)O (g) ΔrH°(0 K) = -0.15 ± 0.9 kcal/molRuscic W1RO
8.27397.4 C6H5N(O)O (g) CH3CH3 (g) → C6H5CH3 (g) CH3N(O)O (g) ΔrH°(0 K) = 0.20 ± 1.0 kcal/molRuscic CBS-n
8.27397.2 C6H5N(O)O (g) CH3CH3 (g) → C6H5CH3 (g) CH3N(O)O (g) ΔrH°(0 K) = -0.43 ± 1.0 kcal/molRuscic G4
6.87397.1 C6H5N(O)O (g) CH3CH3 (g) → C6H5CH3 (g) CH3N(O)O (g) ΔrH°(0 K) = 0.08 ± 1.1 kcal/molRuscic G3X
5.77396.5 C6H5N(O)O (g) NO (g) → C6H5NO (g) ONO (g) ΔrH°(0 K) = 19.87 ± 0.9 kcal/molRuscic W1RO
5.57398.1 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) N2 (g) ΔrH°(298.15 K) = -1476.136 ± 1.43 (×1.834) kcal/molLebedeva 1971, Verevkin 2014
4.87397.3 C6H5N(O)O (g) CH3CH3 (g) → C6H5CH3 (g) CH3N(O)O (g) ΔrH°(0 K) = 0.49 ± 1.3 kcal/molRuscic CBS-n
4.67396.4 C6H5N(O)O (g) NO (g) → C6H5NO (g) ONO (g) ΔrH°(0 K) = 18.62 ± 1.0 kcal/molRuscic CBS-n
4.67396.2 C6H5N(O)O (g) NO (g) → C6H5NO (g) ONO (g) ΔrH°(0 K) = 19.30 ± 1.0 kcal/molRuscic G4
3.87396.1 C6H5N(O)O (g) NO (g) → C6H5NO (g) ONO (g) ΔrH°(0 K) = 19.75 ± 1.1 kcal/molRuscic G3X
2.77396.3 C6H5N(O)O (g) NO (g) → C6H5NO (g) ONO (g) ΔrH°(0 K) = 20.28 ± 1.3 kcal/molRuscic CBS-n
2.57394.1 C6H5NO (g) → C6H5 (g) NO (g) ΔrG°(391 K) = 39.48 ± 0.5 kcal/molPark 1997, Yu 1994a, 3rd Law
2.17393.1 C6H5NO (g) → [C6H5]+ (g) NO (g) ΔrH°(0 K) = 10.607 ± 0.020 eVStevens 2010a

Top 10 species with enthalpies of formation correlated to the ΔfH° 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 Image    ΔfH°(0 K)    ΔfH°(298.15 K) Uncertainty Units Relative
Molecular
Mass
ATcT ID
99.7 NitrobenzeneC6H5N(O)O (g)c1ccc(cc1)[N+](=O)[O-]82.362.3± 1.3kJ/mol123.1094 ±
0.0049
98-95-3*0
34.7 NitrosobenzeneC6H5NO (g)c1ccc(cc1)N=O216.9199.9± 1.2kJ/mol107.1100 ±
0.0048
586-96-9*0
14.2 NitromethaneCH3N(O)O (g)C[N+](=O)[O-]-60.75-74.65± 0.42kJ/mol61.0401 ±
0.0010
75-52-5*0
13.2 Phenylium[C6H5]+ (g)c1cccc[c+]11149.281136.50± 0.85kJ/mol77.1034 ±
0.0048
17333-73-2*0
13.2 Phenylium[C6H5]+ (g, singlet)c1cccc[c+]11149.281136.50± 0.85kJ/mol77.1034 ±
0.0048
17333-73-2*2
12.8 NitromethaneCH3N(O)O (cr,l)C[N+](=O)[O-]-114.10-112.92± 0.40kJ/mol61.0401 ±
0.0010
75-52-5*500
11.4 TolueneC6H5CH3 (g)c1ccc(cc1)C73.3550.06± 0.31kJ/mol92.1384 ±
0.0056
108-88-3*0
11.3 TolueneC6H5CH3 (l)c1ccc(cc1)C19.7812.03± 0.31kJ/mol92.1384 ±
0.0056
108-88-3*500
9.8 PhenylC6H5 (g)c1cccc[c]1352.61339.25± 0.60kJ/mol77.1039 ±
0.0048
2396-01-2*0
9.0 IodobenzeneC6H5I (g)c1ccc(cc1)I178.59162.60± 0.99kJ/mol204.0084 ±
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
0.9467399.2 C6H5N(O)O (cr,l) → C6H5N(O)O (g) ΔrH°(298.15 K) = 55.013 ± 0.1 kJ/molKusano 1971, Verevkin 2014
0.2147398.2 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) N2 (g) ΔrH°(298.15 K) = -6170.83 ± 3.8 (×1.477) kJ/molVerevkin 2014
0.0567398.1 C6H5N(O)O (cr,l) + 25/2 O2 (g) → 12 CO2 (g) + 5 H2O (cr,l) N2 (g) ΔrH°(298.15 K) = -1476.136 ± 1.43 (×1.834) kcal/molLebedeva 1971, Verevkin 2014
0.0377399.4 C6H5N(O)O (cr,l) → C6H5N(O)O (g) ΔrH°(298.15 K) = 55.3 ± 0.5 kJ/molEmmenegger 1999, est unc
0.0057399.3 C6H5N(O)O (cr,l) → C6H5N(O)O (g) ΔrH°(298.15 K) = 56.32 ± 0.5 (×2.594) kJ/molChickos 1995, est unc
0.0057399.5 C6H5N(O)O (cr,l) → C6H5N(O)O (g) ΔrH°(298.15 K) = 55.0 ± 1.3 kJ/molVerevkin 2014, WinTable 2003
0.0037399.1 C6H5N(O)O (cr,l) → C6H5N(O)O (g) ΔrH°(298.15 K) = 13.40 ± 0.40 kcal/molLebedeva 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 21st 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.