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].

Aniline

Formula: C6H5NH2 (cr,l)

CAS RN: 62-53-3

ATcT ID: 62-53-3*500

SMILES: c1ccc(cc1)N

InChI: InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

InChIKey: PAYRUJLWNCNPSJ-UHFFFAOYSA-N

Hills Formula: C6H7N1

2D Image:

Aliases: C6H5NH2; Aniline; Benzenamine; Aminobenzene; Aminophen; Anyvim; Phenylamine; Blue Oil; C.I. 76000; NCI 176889

Relative Molecular Mass: 93.1265 ± 0.0048

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
37.27	31.02	± 0.63	kJ/mol

Top contributors to the provenance of Δ_fH° of C6H5NH2 (cr,l)

The 13 contributors listed below account for 90.4% of the provenance of Δ_fH° of C6H5NH2 (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
37.0	9292.3	2 C6H5NH2 (cr,l) + 31/2 O2 (g) → 12 CO2 (g) + 7 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1621.86 ± 0.48 kcal/mol	Hatton 1962
23.6	9292.2	2 C6H5NH2 (cr,l) + 31/2 O2 (g) → 12 CO2 (g) + 7 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1621.00 ± 0.60 kcal/mol	Huffman 1941, Anderson 1942, est unc
13.3	9292.1	2 C6H5NH2 (cr,l) + 31/2 O2 (g) → 12 CO2 (g) + 7 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1621.62 ± 0.80 kcal/mol	Cole 1951, Anderson 1942, est unc
4.4	9293.1	C6H5NH2 (cr,l) → C6H5NH2 (g)	Δ_rH°(298.15 K) = 55.83 ± 0.56 kJ/mol	Majer 1985
1.6	9290.5	C6H5NH2 (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3NH2 (g)	Δ_rH°(0 K) = 6.34 ± 0.85 kcal/mol	Ruscic W1RO
1.4	9290.2	C6H5NH2 (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3NH2 (g)	Δ_rH°(0 K) = 6.09 ± 0.90 kcal/mol	Ruscic G4
1.4	9290.1	C6H5NH2 (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3NH2 (g)	Δ_rH°(0 K) = 6.32 ± 0.90 kcal/mol	Ruscic G3X
1.4	9290.4	C6H5NH2 (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3NH2 (g)	Δ_rH°(0 K) = 6.45 ± 0.90 kcal/mol	Ruscic CBS-n
1.2	9289.5	C6H5NH2 (g) + CH3CHCH2 (g) → C6H5CH3 (g) + CH2CHNH2 (g)	Δ_rH°(0 K) = -0.30 ± 0.85 kcal/mol	Ruscic W1RO
1.2	9290.3	C6H5NH2 (g) + CH3CH3 (g) → C6H5CH3 (g) + CH3NH2 (g)	Δ_rH°(0 K) = 6.13 ± 1.00 kcal/mol	Ruscic CBS-n
1.1	9289.2	C6H5NH2 (g) + CH3CHCH2 (g) → C6H5CH3 (g) + CH2CHNH2 (g)	Δ_rH°(0 K) = -0.40 ± 0.90 kcal/mol	Ruscic G4
1.1	9289.1	C6H5NH2 (g) + CH3CHCH2 (g) → C6H5CH3 (g) + CH2CHNH2 (g)	Δ_rH°(0 K) = -0.26 ± 0.90 kcal/mol	Ruscic G3X
1.1	9289.4	C6H5NH2 (g) + CH3CHCH2 (g) → C6H5CH3 (g) + CH2CHNH2 (g)	Δ_rH°(0 K) = -0.36 ± 0.90 kcal/mol	Ruscic CBS-n

Top 10 species with enthalpies of formation correlated to the Δ_fH° of C6H5NH2 (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
71.2	Aniline	C6H5NH2 (g)	108.82	86.81	± 0.72	kJ/mol	93.1265 ± 0.0048	62-53-3*0
15.1	Carbonic acid	C(O)(OH)2 (aq, undissoc)		-698.673	± 0.028	kJ/mol	62.0248 ± 0.0012	463-79-6*1000
14.8	Toluene	C6H5CH3 (g)	73.35	50.06	± 0.31	kJ/mol	92.1384 ± 0.0056	108-88-3*0
14.6	Toluene	C6H5CH3 (l)	19.78	12.03	± 0.31	kJ/mol	92.1384 ± 0.0056	108-88-3*500
12.5	Carbon dioxide	CO2 (g)	-393.111	-393.478	± 0.015	kJ/mol	44.00950 ± 0.00100	124-38-9*0
12.3	Carbon dioxide cation	[CO2]+ (g)	936.089	936.924	± 0.017	kJ/mol	44.00895 ± 0.00100	12181-61-2*0
12.2	Succinic acid	(CH2C(O)OH)2 (cr,l)	-918.50	-940.23	± 0.12	kJ/mol	118.0880 ± 0.0034	110-15-6*500
12.1	Benzoic acid	C6H5C(O)OH (cr,l)	-367.34	-384.75	± 0.17	kJ/mol	122.1213 ± 0.0056	65-85-0*500
11.6	Ethenamine	CH2CHNH2 (g)	69.38	54.82	± 0.66	kJ/mol	43.0678 ± 0.0016	593-67-9*0
11.1	Benzylide	[C6H5CH2]- (g)	141.98	123.07	± 0.39	kJ/mol	91.1310 ± 0.0056	18860-15-6*0

Most Influential reactions involving C6H5NH2 (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
0.852	9293.1	C6H5NH2 (cr,l) → C6H5NH2 (g)	Δ_rH°(298.15 K) = 55.83 ± 0.56 kJ/mol	Majer 1985
0.381	9292.3	2 C6H5NH2 (cr,l) + 31/2 O2 (g) → 12 CO2 (g) + 7 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1621.86 ± 0.48 kcal/mol	Hatton 1962
0.244	9292.2	2 C6H5NH2 (cr,l) + 31/2 O2 (g) → 12 CO2 (g) + 7 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1621.00 ± 0.60 kcal/mol	Huffman 1941, Anderson 1942, est unc
0.137	9292.1	2 C6H5NH2 (cr,l) + 31/2 O2 (g) → 12 CO2 (g) + 7 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1621.62 ± 0.80 kcal/mol	Cole 1951, Anderson 1942, 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. 1.176 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.