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].

Diazirine

Formula: CH2(NN) (g)

CAS RN: 157-22-2

ATcT ID: 157-22-2*0

SMILES: C1N=N1

InChI: InChI=1S/CH2N2/c1-2-3-1/h1H2

InChIKey: GKVDXUXIAHWQIK-UHFFFAOYSA-N

Hills Formula: C1H2N2

2D Image:

Aliases: CH2(NN); Diazirine; 3H-Diazirine; 3H-Diazirene; Cyclodiazomethane; H2C(NN); c-CH2N2; cyc-CH2N2

Relative Molecular Mass: 42.04006 ± 0.00082

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
320.4	312.7	± 1.1	kJ/mol

3D Image of CH2(NN) (g)

spin ON spin OFF

Top contributors to the provenance of Δ_fH° of CH2(NN) (g)

The 20 contributors listed below account only for 47.4% of the provenance of Δ_fH° of CH2(NN) (g).
A total of 131 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
7.4	5590.6	CH2(NN) (g) → [CH2]+ (g) + N2 (g)	Δ_rH°(0 K) = 11.109 ± 0.040 eV	Ruscic W1RO
2.8	5589.5	CH2(NN) (g) → CH2 (g, singlet) + N2 (g)	Δ_rH°(0 K) = 26.14 ± 1.50 kcal/mol	Ruscic W1RO
2.7	5583.5	CH2(NN) (g) → NH2CN (g)	Δ_rH°(0 K) = -42.88 ± 1.2 kcal/mol	Ruscic W1RO
2.4	5589.4	CH2(NN) (g) → CH2 (g, singlet) + N2 (g)	Δ_rH°(0 K) = 26.43 ± 1.60 kcal/mol	Ruscic CBS-n
2.4	5589.2	CH2(NN) (g) → CH2 (g, singlet) + N2 (g)	Δ_rH°(0 K) = 25.45 ± 1.60 kcal/mol	Ruscic G4
2.3	5583.2	CH2(NN) (g) → NH2CN (g)	Δ_rH°(0 K) = -42.00 ± 1.3 kcal/mol	Ruscic G4
2.3	5583.4	CH2(NN) (g) → NH2CN (g)	Δ_rH°(0 K) = -42.44 ± 1.3 kcal/mol	Ruscic CBS-n
2.3	5584.5	CH2(NN) (g) → CH2NN (g)	Δ_rH°(0 K) = -10.69 ± 1.2 kcal/mol	Ruscic W1RO
2.2	5590.3	CH2(NN) (g) → [CH2]+ (g) + N2 (g)	Δ_rH°(0 K) = 11.107 ± 0.073 eV	Ruscic G4
2.1	5589.1	CH2(NN) (g) → CH2 (g, singlet) + N2 (g)	Δ_rH°(0 K) = 24.94 ± 1.72 kcal/mol	Ruscic G3X
2.1	5590.5	CH2(NN) (g) → [CH2]+ (g) + N2 (g)	Δ_rH°(0 K) = 11.137 ± 0.075 eV	Ruscic CBS-n
2.0	5583.1	CH2(NN) (g) → NH2CN (g)	Δ_rH°(0 K) = -43.46 ± 1.4 kcal/mol	Ruscic G3X
1.9	5584.4	CH2(NN) (g) → CH2NN (g)	Δ_rH°(0 K) = -11.68 ± 1.3 kcal/mol	Ruscic CBS-n
1.9	5584.2	CH2(NN) (g) → CH2NN (g)	Δ_rH°(0 K) = -10.85 ± 1.3 kcal/mol	Ruscic G4
1.7	5544.1	NH2CN (cr) → NH2CN (g)	Δ_rH°(298.15 K) = 75.2 ± 1.5 kJ/mol	de Wit 1983a, est unc
1.7	5584.1	CH2(NN) (g) → CH2NN (g)	Δ_rH°(0 K) = -11.58 ± 1.4 kcal/mol	Ruscic G3X
1.6	5585.6	CH2(NN) (g) → HC(NN) (g, 2A2) + H (g)	Δ_rH°(0 K) = 93.07 ± 1.50 kcal/mol	Puzzarini 2004, est unc
1.6	5585.5	CH2(NN) (g) → HC(NN) (g, 2A2) + H (g)	Δ_rH°(0 K) = 92.53 ± 1.50 kcal/mol	Ruscic W1RO
1.5	5583.3	CH2(NN) (g) → NH2CN (g)	Δ_rH°(0 K) = -42.50 ± 1.6 kcal/mol	Ruscic CBS-n
1.3	5590.2	CH2(NN) (g) → [CH2]+ (g) + N2 (g)	Δ_rH°(0 K) = 11.063 ± 0.093 eV	Ruscic G3X

Top 10 species with enthalpies of formation correlated to the Δ_fH° of CH2(NN) (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
48.6	Diazirenide	[HC(NN)]- (g, singlet)	454.7	452.0	± 1.5	kJ/mol	41.03267 ± 0.00082	130614-84-5*2
48.6	Diazirenide	[HC(NN)]- (g)	454.7	452.0	± 1.5	kJ/mol	41.03267 ± 0.00082	130614-84-5*0
43.6	1H-Diazirene	CH(NHN) (g)	405.2	398.1	± 1.5	kJ/mol	42.04006 ± 0.00082	157-23-3*0
42.5	3-Diaziridinylidene	C(NHNH) (g, anti)	523.0	516.2	± 2.0	kJ/mol	42.04006 ± 0.00082	85513-79-7*1
42.5	3-Diaziridinylidene	C(NHNH) (g)	523.0	516.2	± 2.0	kJ/mol	42.04006 ± 0.00082	85513-79-7*0
38.3	3H-Diazirine cation	[CH2(NN)]+ (g)	1327.5	1321.9	± 1.7	kJ/mol	42.03951 ± 0.00082	796039-16-2*0
37.4	Isocyanamide	NH2NC (g)	328.4	322.5	± 1.5	kJ/mol	42.04006 ± 0.00082	4702-38-9*0
34.2	Diazomethane	CH2NN (g)	273.53	267.26	± 0.86	kJ/mol	42.04006 ± 0.00082	334-88-3*0
34.1	Diazomethane cation	[CH2NN]+ (g)	1141.84	1135.56	± 0.87	kJ/mol	42.03951 ± 0.00082	58852-13-4*0
33.8	1H-Diazirene cation	[CH(NHN)]+ (g)	1333.5	1326.5	± 1.9	kJ/mol	42.03951 ± 0.00082	157-23-30

Most Influential reactions involving CH2(NN) (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
0.172	5581.5	CH2(NN) (g) → [CH2(NN)]+ (g)	Δ_rH°(0 K) = 10.440 ± 0.040 eV	Ruscic W1RO
0.158	5588.5	CH2(NN) (g) + [CH3CH2NH]- (g) → [HC(NN)]- (g, singlet) + CH3CH2NH2 (g)	Δ_rH°(0 K) = -0.25 ± 0.8 kcal/mol	Ruscic W1RO
0.123	5586.5	CH2(NN) (g) → [HC(NN)]- (g) + H+ (g)	Δ_rH°(0 K) = 397.40 ± 0.90 kcal/mol	Ruscic W1RO
0.122	5606.5	C(NHNH) (g, anti) → CH2(NN) (g)	Δ_rH°(0 K) = -48.01 ± 1.2 kcal/mol	Ruscic W1RO
0.110	5581.6	CH2(NN) (g) → [CH2(NN)]+ (g)	Δ_rH°(0 K) = 10.45 ± 0.05 eV	Puzzarini 2004, est unc
0.103	5606.2	C(NHNH) (g, anti) → CH2(NN) (g)	Δ_rH°(0 K) = -48.61 ± 1.3 kcal/mol	Ruscic G4
0.103	5606.4	C(NHNH) (g, anti) → CH2(NN) (g)	Δ_rH°(0 K) = -48.71 ± 1.3 kcal/mol	Ruscic CBS-n
0.101	5588.4	CH2(NN) (g) + [CH3CH2NH]- (g) → [HC(NN)]- (g, singlet) + CH3CH2NH2 (g)	Δ_rH°(0 K) = 0.30 ± 1.0 kcal/mol	Ruscic CBS-n
0.101	5588.2	CH2(NN) (g) + [CH3CH2NH]- (g) → [HC(NN)]- (g, singlet) + CH3CH2NH2 (g)	Δ_rH°(0 K) = 0.11 ± 1.0 kcal/mol	Ruscic G4
0.089	5606.1	C(NHNH) (g, anti) → CH2(NN) (g)	Δ_rH°(0 K) = -48.30 ± 1.4 kcal/mol	Ruscic G3X
0.081	5617.5	NH2NC (g) → CH2(NN) (g)	Δ_rH°(0 K) = -1.96 ± 1.2 kcal/mol	Ruscic W1RO
0.077	5595.5	CH(NHN) (g) → CH2(NN) (g)	Δ_rH°(0 K) = -20.07 ± 1.2 kcal/mol	Ruscic W1RO
0.075	5590.6	CH2(NN) (g) → [CH2]+ (g) + N2 (g)	Δ_rH°(0 K) = 11.109 ± 0.040 eV	Ruscic W1RO
0.070	5588.1	CH2(NN) (g) + [CH3CH2NH]- (g) → [HC(NN)]- (g, singlet) + CH3CH2NH2 (g)	Δ_rH°(0 K) = -0.32 ± 1.2 kcal/mol	Ruscic G3X
0.069	5617.2	NH2NC (g) → CH2(NN) (g)	Δ_rH°(0 K) = -2.30 ± 1.3 kcal/mol	Ruscic G4
0.069	5617.4	NH2NC (g) → CH2(NN) (g)	Δ_rH°(0 K) = -1.87 ± 1.3 kcal/mol	Ruscic CBS-n
0.068	5606.3	C(NHNH) (g, anti) → CH2(NN) (g)	Δ_rH°(0 K) = -48.30 ± 1.6 kcal/mol	Ruscic CBS-n
0.066	5595.2	CH(NHN) (g) → CH2(NN) (g)	Δ_rH°(0 K) = -20.45 ± 1.3 kcal/mol	Ruscic G4
0.066	5595.4	CH(NHN) (g) → CH2(NN) (g)	Δ_rH°(0 K) = -20.51 ± 1.3 kcal/mol	Ruscic CBS-n
0.060	5588.3	CH2(NN) (g) + [CH3CH2NH]- (g) → [HC(NN)]- (g, singlet) + CH3CH2NH2 (g)	Δ_rH°(0 K) = -0.84 ± 1.3 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.