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].

Pyridine

Formula: N(CHCHCHCHCH) (g)

CAS RN: 110-86-1

ATcT ID: 110-86-1*0

SMILES: c1ccncc1

InChI: InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H

InChIKey: JUJWROOIHBZHMG-UHFFFAOYSA-N

Hills Formula: C5H5N1

2D Image:

Aliases: N(CHCHCHCHCH); Pyridine; Azabenzene; Azine; CP 32; NSC 141574; NSC 406123; C5NH5

Relative Molecular Mass: 79.0999 ± 0.0040

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
157.34	140.54	± 0.40	kJ/mol

3D Image of N(CHCHCHCHCH) (g)

spin ON spin OFF

Top contributors to the provenance of Δ_fH° of N(CHCHCHCHCH) (g)

The 17 contributors listed below account for 90.5% of the provenance of Δ_fH° of N(CHCHCHCHCH) (g).

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
65.0	6932.1	2 N(CHCHCHCHCH) (cr,l) + 25/2 O2 (g) → 10 CO2 (g) + 5 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1329.92 ± 0.20 kcal/mol	Hubbard 1961
6.5	6933.1	N(CHCHCHCHCH) (cr,l) → N(CHCHCHCHCH) (g)	Δ_rH°(298.15 K) = 9.656 ± 0.04 kcal/mol	Andon 1957, est unc
5.0	6932.2	2 N(CHCHCHCHCH) (cr,l) + 25/2 O2 (g) → 10 CO2 (g) + 5 H2O (cr,l) + N2 (g)	Δ_rH°(298.15 K) = -1330.01 ± 0.72 kcal/mol	Cox 1954
2.2	6921.6	N(CHCHCHCHCH) (g) → 5 C (g) + N (g) + 5 H (g)	Δ_rH°(0 K) = 1183.35 ± 0.60 kcal/mol	Karton 2009a
1.6	6933.2	N(CHCHCHCHCH) (cr,l) → N(CHCHCHCHCH) (g)	Δ_rH°(298.15 K) = 9.61 ± 0.08 kcal/mol	McCullough 1957, ThermoData 2004
1.0	6926.5	N(CHCHCHCHCH) (g) + HCCH (g) → C6H6 (g) + HCN (g)	Δ_rH°(0 K) = -37.24 ± 0.85 kcal/mol	Ruscic W1RO
0.9	6926.1	N(CHCHCHCHCH) (g) + HCCH (g) → C6H6 (g) + HCN (g)	Δ_rH°(0 K) = -36.90 ± 0.90 kcal/mol	Ruscic G3X
0.9	6926.2	N(CHCHCHCHCH) (g) + HCCH (g) → C6H6 (g) + HCN (g)	Δ_rH°(0 K) = -37.07 ± 0.90 kcal/mol	Ruscic G4
0.9	6926.4	N(CHCHCHCHCH) (g) + HCCH (g) → C6H6 (g) + HCN (g)	Δ_rH°(0 K) = -37.93 ± 0.90 kcal/mol	Ruscic CBS-n
0.9	2134.7	C (graphite) + O2 (g) → CO2 (g)	Δ_rH°(298.15 K) = -393.464 ± 0.024 kJ/mol	Hawtin 1966, note CO2e
0.8	6927.5	N(CHCHCHCHCH) (g) + CH2CH2 (g) → C6H6 (g) + CH2NH (g)	Δ_rH°(0 K) = -5.11 ± 0.9 kcal/mol	Ruscic W1RO
0.7	6926.3	N(CHCHCHCHCH) (g) + HCCH (g) → C6H6 (g) + HCN (g)	Δ_rH°(0 K) = -36.92 ± 1.00 kcal/mol	Ruscic CBS-n
0.7	6928.5	N(CHCHCHCHCH) (g) + CH3CHCH2 (g) → C6H6 (g) + CH3NCH2 (g)	Δ_rH°(0 K) = 0.81 ± 0.85 kcal/mol	Ruscic W1RO
0.7	6933.3	N(CHCHCHCHCH) (cr,l) → N(CHCHCHCHCH) (g)	Δ_rH°(298.15 K) = 40.15 ± 0.50 kJ/mol	WinTable 2003, est unc
0.7	6927.4	N(CHCHCHCHCH) (g) + CH2CH2 (g) → C6H6 (g) + CH2NH (g)	Δ_rH°(0 K) = -5.07 ± 1.0 kcal/mol	Ruscic CBS-n
0.7	6927.2	N(CHCHCHCHCH) (g) + CH2CH2 (g) → C6H6 (g) + CH2NH (g)	Δ_rH°(0 K) = -4.80 ± 1.0 kcal/mol	Ruscic G4
0.6	6928.2	N(CHCHCHCHCH) (g) + CH3CHCH2 (g) → C6H6 (g) + CH3NCH2 (g)	Δ_rH°(0 K) = 0.81 ± 0.90 kcal/mol	Ruscic G4

Top 10 species with enthalpies of formation correlated to the Δ_fH° of N(CHCHCHCHCH) (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
93.4	Pyridine	N(CHCHCHCHCH) (cr,l)	102.24	100.21	± 0.38	kJ/mol	79.0999 ± 0.0040	110-86-1*500
66.0	Pyridiniumyl	[N(CHCHCHCHCH)]+ (g)	1051.33	1035.38	± 0.61	kJ/mol	79.0994 ± 0.0040	16399-94-3*0
31.3	Pyridinium	[NH(CHCHCHCHCH)]+ (g)	761.7	740.8	± 1.3	kJ/mol	80.1073 ± 0.0040	16969-45-2*0
18.4	Carbonic acid	C(O)(OH)2 (aq, undissoc)		-698.995	± 0.028	kJ/mol	62.0248 ± 0.0012	463-79-6*1000
16.5	Carbon dioxide	CO2 (g)	-393.110	-393.476	± 0.015	kJ/mol	44.00950 ± 0.00100	124-38-9*0
16.3	Carbon dioxide cation	[CO2]+ (g)	936.090	936.925	± 0.017	kJ/mol	44.00895 ± 0.00100	12181-61-2*0
16.1	Benzene	C6H6 (g)	100.71	83.20	± 0.21	kJ/mol	78.1118 ± 0.0048	71-43-2*0
16.1	Benzene cation	[C6H6]+ (g)	992.61	976.14	± 0.21	kJ/mol	78.1113 ± 0.0048	34504-50-2*0
16.0	Benzene	C6H6 (cr,l)	50.81	49.26	± 0.21	kJ/mol	78.1118 ± 0.0048	71-43-2*500
15.2	Benzoic acid	C6H5C(O)OH (cr,l)	-367.31	-384.73	± 0.17	kJ/mol	122.1213 ± 0.0056	65-85-0*500

Most Influential reactions involving N(CHCHCHCHCH) (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
0.883	6922.1	N(CHCHCHCHCH) (g) → [N(CHCHCHCHCH)]+ (g)	Δ_rH°(0 K) = 9.266 ± 0.005 eV	El-Sayed 1961, est unc
0.720	6933.1	N(CHCHCHCHCH) (cr,l) → N(CHCHCHCHCH) (g)	Δ_rH°(298.15 K) = 9.656 ± 0.04 kcal/mol	Andon 1957, est unc
0.432	6923.5	[N(CHCHCHCHCH)]- (g) → N(CHCHCHCHCH) (g)	Δ_rH°(0 K) = -0.620 ± 0.050 eV	Ruscic W1RO
0.360	6936.2	[NH(CHCHCHCHCH)]+ (g) + NH3 (g) → N(CHCHCHCHCH) (g) + [NH4]+ (g)	Δ_rG°(350 K) = 80.5 ± 2.0 kJ/mol	Hunter 1998, Taft 1986, est unc
0.290	6923.2	[N(CHCHCHCHCH)]- (g) → N(CHCHCHCHCH) (g)	Δ_rH°(0 K) = -0.535 ± 0.061 eV	Ruscic G4
0.180	6933.2	N(CHCHCHCHCH) (cr,l) → N(CHCHCHCHCH) (g)	Δ_rH°(298.15 K) = 9.61 ± 0.08 kcal/mol	McCullough 1957, ThermoData 2004
0.149	6923.1	[N(CHCHCHCHCH)]- (g) → N(CHCHCHCHCH) (g)	Δ_rH°(0 K) = -0.603 ± 0.085 eV	Ruscic G3X
0.128	6936.7	[NH(CHCHCHCHCH)]+ (g) + NH3 (g) → N(CHCHCHCHCH) (g) + [NH4]+ (g)	Δ_rH°(0 K) = 18.58 ± 0.8 kcal/mol	Ruscic W1RO
0.127	6923.3	[N(CHCHCHCHCH)]- (g) → N(CHCHCHCHCH) (g)	Δ_rH°(0 K) = -0.606 ± 0.092 eV	Ruscic CBS-n
0.103	6935.5	[NH(CHCHCHCHCH)]+ (g) → N(CHCHCHCHCH) (g) + H+ (g)	Δ_rH°(0 K) = 221.15 ± 0.90 kcal/mol	Ruscic W1RO
0.102	6929.9	N(CHCHCHCHCH) (g) → [CH2C(CHCH)]+ (g) + HCN (g)	Δ_rH°(0 K) = 11.973 ± 0.040 eV	Ruscic W1RO
0.082	6936.6	[NH(CHCHCHCHCH)]+ (g) + NH3 (g) → N(CHCHCHCHCH) (g) + [NH4]+ (g)	Δ_rH°(0 K) = 18.06 ± 1.0 kcal/mol	Ruscic CBS-n
0.082	6936.4	[NH(CHCHCHCHCH)]+ (g) + NH3 (g) → N(CHCHCHCHCH) (g) + [NH4]+ (g)	Δ_rH°(0 K) = 18.21 ± 1.0 kcal/mol	Ruscic G4
0.080	6933.3	N(CHCHCHCHCH) (cr,l) → N(CHCHCHCHCH) (g)	Δ_rH°(298.15 K) = 40.15 ± 0.50 kJ/mol	WinTable 2003, est unc
0.061	6936.1	[NH(CHCHCHCHCH)]+ (g) + NH3 (g) → N(CHCHCHCHCH) (g) + [NH4]+ (g)	Δ_rH°(0 K) = 0.82 ± 0.05 eV	Chyall 1995
0.057	6936.3	[NH(CHCHCHCHCH)]+ (g) + NH3 (g) → N(CHCHCHCHCH) (g) + [NH4]+ (g)	Δ_rH°(0 K) = 17.71 ± 1.2 kcal/mol	Ruscic G3X
0.048	6936.5	[NH(CHCHCHCHCH)]+ (g) + NH3 (g) → N(CHCHCHCHCH) (g) + [NH4]+ (g)	Δ_rH°(0 K) = 17.50 ± 1.3 kcal/mol	Ruscic CBS-n
0.044	6928.5	N(CHCHCHCHCH) (g) + CH3CHCH2 (g) → C6H6 (g) + CH3NCH2 (g)	Δ_rH°(0 K) = 0.81 ± 0.85 kcal/mol	Ruscic W1RO
0.039	6928.1	N(CHCHCHCHCH) (g) + CH3CHCH2 (g) → C6H6 (g) + CH3NCH2 (g)	Δ_rH°(0 K) = 1.05 ± 0.90 kcal/mol	Ruscic G3X
0.039	6928.4	N(CHCHCHCHCH) (g) + CH3CHCH2 (g) → C6H6 (g) + CH3NCH2 (g)	Δ_rH°(0 K) = 0.75 ± 0.90 kcal/mol	Ruscic CBS-n

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.