N-Nitrosodimethylamine
- Formula: C2H6N2O
- Molecular weight: 74.0818
- IUPAC Standard InChI: InChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3
- IUPAC Standard InChIKey: UMFJAHHVKNCGLG-UHFFFAOYSA-N
- CAS Registry Number: 62-75-9
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Isotopologues:
- Other names: Methanamine, N-methyl-N-nitroso-; Dimethylamine, N-nitroso-; Dimethylnitrosamine; DMN; DMNA; N-Nitroso-N,N-Dimethylamine; (CH3)2NNO; Dimethylnitrosamin; Dimethylnitrosoamine; N-Methyl-N-nitrosomethanamine; N,N-Dimethylnitrosamine; NDMA; Nitrosodimethylamine; Rcra waste number P082; NSC 23226
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Gas phase ion energetics data
Go To: Top, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.69 | PE | White, Colton, et al., 1975 | LLK |
| 9.05 | PE | Kobayashi, 1975 | Vertical value; LLK |
| 9.09 | PE | Battiste, Davis, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H6N+ | 10.3 ± 0.05 | NO? | EI | Fisher and Henderson, 1967 | RDSH |
| C2H6N+ | 10.9 ± 0.1 | NO? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
| NO+ | 11.1 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
De-protonation reactions
C2H5N2O- + =
By formula: C2H5N2O- + H+ = C2H6N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 380.9 ± 2.1 | kcal/mol | G+TS | Ingemann and Nibbering, 1985 | gas phase; The experimental dHf(Me2NNO) { Korsunskii, Pepekin, et al., 1967} is incorrect: JEB, manuscript in preparation; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 373.8 ± 2.0 | kcal/mol | IMRE | Ingemann and Nibbering, 1985 | gas phase; The experimental dHf(Me2NNO) { Korsunskii, Pepekin, et al., 1967} is incorrect: JEB, manuscript in preparation; value altered from reference due to change in acidity scale; B |
IR Spectrum
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
- LIQUID (NEAT) $$ PURITY - ANALYTICAL $$ SEE SPECTRUN NO. 4837 FOR "SOLUTION" RUN; PERKIN-ELMER 180 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (11% IN CCl4 FOR 3800-1300, 2% IN CS2 FOR 1300-650, 11% IN CCl4 FOR 650-250 CM-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 697 |
| NIST MS number | 229457 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 708. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Methyl Silicone | 708. | Zenkevich, 1999 | Program: not specified |
References
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
White, Colton, et al., 1975
White, M.G.; Colton, R.J.; Lee, T.H.; Rabalais, J.W.,
Electronic structure of N,N-dimethylnitramine and N,N-dimethylnitrosamine from X-ray and uv electron spectroscopy,
Chem. Phys., 1975, 8, 391. [all data]
Kobayashi, 1975
Kobayashi, T.,
Photoelectron spectra of N, N-dimethylnitrosamine and related compounds,
Russ. J. Phys. Chem., 1975, 97, 269. [all data]
Battiste, Davis, et al., 1975
Battiste, D.R.; Davis, L.P.; Nauman, R.V.,
Photoelectron spectroscopy and quantum chemical analysis of some «N»-nitrosamines,
J. Am. Chem. Soc., 1975, 97, 5071. [all data]
Fisher and Henderson, 1967
Fisher, I.P.; Henderson, E.,
Mass spectrometry of free radicals,
J. Chem. Soc. Faraday Trans., 1967, 63, 1342. [all data]
Gowenlock, Jones, et al., 1961
Gowenlock, B.G.; Jones, P.P.; Majer, J.R.,
Bond dissociation energies in some molecules containing alkyl substituted CH3, NH2, and OH,
J. Chem. Soc. Faraday Trans., 1961, 57, 23. [all data]
Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M.,
Gas phase chemistry of dipole stabilized carbanions derived from N,N-dimethylthioformamide and N,N-dimethylnitrosamine,
Acta Chem. Scand., Ser. B, 1985, 39, 697. [all data]
Korsunskii, Pepekin, et al., 1967
Korsunskii, B.L.; Pepekin, V.I.; Lebedev, Yu.A.; Apin, A.Ya.,
Bull. Acad. Sci. USSR Div. Chem. Sci., 1967, 509. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Zenkevich, 1999
Zenkevich, I.G.,
Precalculation of Gas Chromatographic Retention Indices of Organic Compounds from Boiling Points of their Structural Analogues,
Zh. Struct. Khim., 1999, 40, 1, 121-130. [all data]
Notes
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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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