Methanamine, N-methyl-N-nitro-
- Formula: C2H6N2O2
- Molecular weight: 90.0812
- IUPAC Standard InChIKey: XRWKADIRZXTTLH-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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 | -1.2 ± 0.3 | kcal/mol | Ccb | Matyushin, V'yunova, et al., 1971 | see Korsunsky, Pepkin, et al., 1967 |
Phase change data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 460.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 345.45 | K | N/A | Bruhl, 1897 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 16.70 | kcal/mol | V | Bradley, Cotson, et al., 1952 | ALS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.7 | 319. | DBM | Stephen, Bradley, et al., 1952 | Based on data from 315. to 324. K. See also Pedley and Rylance, 1977.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.125 | 331.5 | DSC | Zeman, 1997 | AC |
9.001 | 327. | N/A | Oyumi and Brill, 1987 | AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 198.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 190.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.53 | PE | White, Colton, et al., 1975 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H6N+ | 11. ± 10. | NO2? | EI | Fisher and Henderson, 1967 | RDSH |
C2H6N+ | 11.1 ± 0.1 | NO2? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
NO2+ | 14.6 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, UV/Visible spectrum, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | T. BRYCE UNILEVER RESEARCH COLWORTH/WELWYN, BEDFORD U.K. |
NIST MS number | 748 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, 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.
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
Source | Andreev, et al., 1978 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 22255 |
Instrument | SFD-2 |
Melting point | 58 |
Boiling point | 187 |
References
Go To: Top, Gas 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]
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
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.