Methanamine, N-methyl-N-nitro-

• Formula: C₂H₆N₂O₂
• Molecular weight: 90.0812
• IUPAC Standard InChI: InChI=1S/C2H6N2O2/c1-3(2)4(5)6/h1-2H3 Copy

  
• IUPAC Standard InChIKey: XRWKADIRZXTTLH-UHFFFAOYSA-N Copy
• CAS Registry Number: 4164-28-7
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Dimethylnitramine; Dimethylamine, N-nitro-; s-N,N-Dimethyl nitramine; Dimethylnitroamine; N-Nitrodimethylamine; N,N-Dimethylnitramine; (CH3)2NNO2; Dimethylnitramin; DMNO; DMN; N-Nitro-DMA; NSC 137860
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
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

Appearance energy determinations

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Matyushin, V'yunova, et al., 1971
Matyushin, Yu.N.; V'yunova, I.B.; Pepekin, V.I.; Apin, A.Ya., Enthalpy of formation of the piperidyl radical, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971, 2320-2323. [all data]

Korsunsky, Pepkin, et al., 1967
Korsunsky, B.L.; Pepkin, V.I.; Lebedev, Yu.A.; Apin, A.Ya., Thermochemical and kinetic investigation of N,N-dimethylnitrosoamine, Izv. Akad. Nauk SSSR, Ser. Khim., 1967, 525-528. [all data]

Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Quincey, P.G.; Springall, H.D., Heats of combustion and molecular structure. Part IV. Aliphatic nitroalkanes and nitric esters, J. Chem. Soc., 1958, 958-962. [all data]

Handrick, 1956
Handrick, G.R., Report of the study of pure explosive compounds. Part IV. Calculation of heat of combustion of organic compounds from structural features and calculation of power of high explosives, Rpt. C-58247 for the Office of the Chief of Ordnance, contract DA-19-020-ORD-47 by the Arthur D. Little, Inc., Cambridge, MA, 1956, 467-573. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Bruhl, 1897
Bruhl, J.W., Spectrochemistry of nitrogen containing compounds V, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1897, 22, 373. [all data]

Bradley, Cotson, et al., 1952
Bradley, R.S.; Cotson, S.; Cox, E.G., The determination of vapour pressures of the order of 1 mm of mercury by a mnodification of Smith and Menzie's method. The vapour pressure of dimethylnitramine, J. Chem. Soc., 1952, 740-741. [all data]

Stephen, Bradley, et al., 1952
Stephen, Alistair M.; Bradley, R.S.; Cotson, S.; Cox, E.G.; Gerrard, W.; Thrush, A.M.; Fairfull, A.E.S.; Lowe, J.L.; Peak, D.A., Notes, J. Chem. Soc., 1952, 738, https://doi.org/10.1039/jr9520000738 . [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [all data]

Zeman, 1997
Zeman, Svatopluk, Some predictions in the field of the physical thermal stability of nitramines, Thermochimica Acta, 1997, 302, 1-2, 11-16, https://doi.org/10.1016/S0040-6031(96)03101-2 . [all data]

Oyumi and Brill, 1987
Oyumi, Y.; Brill, T.B., Thermal decomposition of energetic materials. 23. Thermochemical differentiation of cyclic and acyclic nitramines by their phase transitions, Thermochim. Acta, 1987, 116, 125-130. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [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]

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]

Andreev, et al., 1978
Andreev, S.A., et al., Zhur. Organ. Khim., 1978, 14, 240. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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