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:
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Gas phase ion energetics data
Go To: Top, 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 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| CHN2+ | 14.2 ± 0.1 | H | EI | Paulett and Ettinger, 1963 | RDSH |
| CH2+ | 11.0 ± 0.1 | N2 | EI | Paulett and Ettinger, 1963 | RDSH |
De-protonation reactions
CHN2- + =
By formula: CHN2- + H+ = CH2N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1681. ± 13. | kJ/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° | 1648. ± 13. | kJ/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° | 1633. ± 13. | kJ/mol | G+TS | Broadus and Kass, 1999 | gas phase; Betweeen D2O, fluorobenzene; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1598. ± 13. | kJ/mol | IMRB | Broadus and Kass, 1999 | gas phase; Betweeen D2O, fluorobenzene; B |
References
Go To: Top, 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.
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
Paulett, G.S.; Ettinger, R.,
Mass spectra and appearance potentials of diazirine and diazomethane,
J. Chem. Phys., 1963, 39, 825. [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]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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