3H-Diazirine
- Formula: CH2N2
- Molecular weight: 42.0400
- IUPAC Standard InChI: InChI=1S/CH2N2/c1-2-3-1/h1H2
- IUPAC Standard InChIKey: GKVDXUXIAHWQIK-UHFFFAOYSA-N
- CAS Registry Number: 157-22-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 63.85 | kcal/mol | Ion | Laufer and Okabe, 1972 | 66>Hf-gas-(298) >61.7 kcal/mol |
| ΔfH°gas | 79.3 ± 2.3 | kcal/mol | Ion | Paulett and Ettinger, 1963 | Mass spectra |
Reaction thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: John E. Bartmess
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
CHN2- + =
By formula: CHN2- + H+ = CH2N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 401.7 ± 3.1 | kcal/mol | G+TS | Kroeker and Kass, 1990 | gas phase; Between MeNH2, EtNH2. The expt dHf(diazirine) disagrees with numerous l calculations by -14 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 394.0 ± 3.0 | kcal/mol | IMRB | Kroeker and Kass, 1990 | gas phase; Between MeNH2, EtNH2. The expt dHf(diazirine) disagrees with numerous l calculations by -14 kcal/mol |
+
=
By formula: CH3N2- + H+ = CH2N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 390.2 ± 3.1 | kcal/mol | G+TS | Broadus and Kass, 1999 | gas phase; Betweeen D2O, fluorobenzene |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 382.0 ± 3.0 | kcal/mol | IMRB | Broadus and Kass, 1999 | gas phase; Betweeen D2O, fluorobenzene |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to CH2N2+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.3 | PE | Robin, Brundle, et al., 1972 | LLK |
| 10.18 ± 0.05 | EI | Paulett and Ettinger, 1963, 2 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| CHN2+ | 14.2 ± 0.1 | H | EI | Paulett and Ettinger, 1963, 2 | RDSH |
| CH2+ | 11.0 ± 0.1 | N2 | EI | Paulett and Ettinger, 1963, 2 | RDSH |
De-protonation reactions
CHN2- + =
By formula: CHN2- + H+ = CH2N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 401.7 ± 3.1 | kcal/mol | G+TS | Kroeker and Kass, 1990 | gas phase; Between MeNH2, EtNH2. The expt dHf(diazirine) disagrees with numerous l calculations by -14 kcal/mol; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 394.0 ± 3.0 | kcal/mol | IMRB | Kroeker and Kass, 1990 | gas phase; Between MeNH2, EtNH2. The expt dHf(diazirine) disagrees with numerous l calculations by -14 kcal/mol; B |
+
=
By formula: CH3N2- + H+ = CH2N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 390.2 ± 3.1 | kcal/mol | G+TS | Broadus and Kass, 1999 | gas phase; Betweeen D2O, fluorobenzene; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 382.0 ± 3.0 | kcal/mol | IMRB | Broadus and Kass, 1999 | gas phase; Betweeen D2O, fluorobenzene; B |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Laufer and Okabe, 1972
Laufer, A.H.; Okabe, H.,
Determination of the heat of formation of diazirine by photon impact,
J. Phys. Chem., 1972, 76, 3504-3507. [all data]
Paulett and Ettinger, 1963
Paulett, G.S.; Ettinger, R.,
Mass spectra and appearance potentials of diazirine and diazomethane,
J. Chem. Phys., 1963, 39, 825-827. [all data]
Kroeker and Kass, 1990
Kroeker, R.L.; Kass, S.R.,
Diazirinyl Anion: A Cyclic 4-pi Electron System,
J. Am. Chem. Soc., 1990, 112, 24, 9024, https://doi.org/10.1021/ja00180a082
. [all data]
Broadus and Kass, 1999
Broadus, K.M.; Kass, S.R.,
Conjugate Base of a Cyclic Hydrazine: Formation and Energetics of N-Diaziridyl Anion,
Int. J. Mass Spectrom., 1999, 185, 179, https://doi.org/10.1016/S1387-3806(98)14164-7
. [all data]
Robin, Brundle, et al., 1972
Robin, M.B.; Brundle, C.R.; Kuebler, N.A.; Ellison, G.B.; Wiberg, K.B.,
Photoelectron spectra of small rings. IV. The unsaturated three-membered rings,
J. Chem. Phys., 1972, 57, 1758. [all data]
Paulett and Ettinger, 1963, 2
Paulett, G.S.; Ettinger, R.,
Mass spectra and appearance potentials of diazirine and diazomethane,
J. Chem. Phys., 1963, 39, 825. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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