N-Nitrosodimethylamine
- Formula: C2H6N2O
- Molecular weight: 74.0818
- 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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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -1650. | kJ/mol | Ccb | Swientoslawski, 1910 |
Phase change 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: Robert L. Brown and Stephen E. Stein
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference |
---|---|---|
426.2 | 1.03 | Aldrich Chemical Company Inc., 1990 |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 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° | 1594. ± 8.8 | kJ/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° | 1564. ± 8.4 | kJ/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 |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change 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: 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 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Swientoslawski, 1910
Swientoslawski, W.,
Thermochemische Untersuchungen der organischen Verbindungen. Dritte Mitteilung. Stickstoffhaltige Verbindungen.,
Z. Phys. Chem., 1910, 72, 49-83. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid 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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