Hydrazine, 1,1-dimethyl-
- Formula: C2H8N2
- Molecular weight: 60.0983
- IUPAC Standard InChIKey: RHUYHJGZWVXEHW-UHFFFAOYSA-N
- CAS Registry Number: 57-14-7
- 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. - Species with the same structure:
- Other names: as-Dimethylhydrazine; Dimazin; Dimazine; Hydrazine, N,N-dimethyl-; N,N-Dimethylhydrazine; UDMH; 1,1-Dimethylhydrazine; (CH3)2NNH2; Unsym-dimethylhydrazine; Dimethylhydrazine, unsymmetrical; Dimethylhydrazine, unsym.; 1,1-Dimethylhydrazin; asymmetric Dimethylhydrazine; uns-Dimethylhydrazine; Niesymetryczna dwu metylohydrazyna; Rcra waste number U098; UN 1163; Unsymmetrical dimethylhydrazine; u-Dimethylhydrazine; gem-Dimethylhydrazine; NSC 60517
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Phase change data
Go To: Top, 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 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 337.1 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 336.2 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 216. | K | N/A | McMillan, 1967 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 215.95 | K | N/A | Aston, Wood, et al., 1953 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.418 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 8.37 ± 0.04 | kcal/mol | V | Aston, Wood, et al., 1953, 2 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
336.2 | 0.991 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.3659 | 298.15 | N/A | Aston, Wood, et al., 1953, 3 | P = 20.90 kPa; DH |
7.780 | 336.2 | N/A | Majer and Svoboda, 1985 | |
8.15 | 284. | N/A | Bourret-Courchesne, Ye, et al., 2000 | Based on data from 267. to 303. K.; AC |
8.72 | 277. | A | Stephenson and Malanowski, 1987 | Based on data from 238. to 292. K. See also Aston, Wood, et al., 1953, 3 and Boublik, Fried, et al., 1984.; AC |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
28.06 | 298.15 | Aston, Wood, et al., 1953, 3 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
237.74 to 293.08 | 4.70745 | 1388.51 | -40.613 | Aston, Wood, et al., 1953, 3 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.40741 | 215.95 | Aston, Wood, et al., 1953, 3 | DH |
2.407 | 216. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.15 | 215.95 | Aston, Wood, et al., 1953, 3 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.29 ± 0.05 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 221.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 213.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.29 ± 0.05 | EQ | Mautner(Meot-Ner), Nelsen, et al., 1984 | LBLHLM |
8.05 ± 0.05 | PE | Vovna, Vilesov, et al., 1975 | LLK |
8.28 | PE | Bodor, Dewar, et al., 1970 | RDSH |
7.67 ± 0.05 | PI | Akopyan and Vilesov, 1963 | RDSH |
7.46 ± 0.02 | PI | Akopyan, Vilesov, et al., 1963 | RDSH |
8.1 ± 0.1 | EI | Dibeler, Franklin, et al., 1959 | RDSH |
8.82 | PE | Rademacher, 1975 | Vertical value; LLK |
8.85 | PE | Kimura, Katsumata, et al., 1975 | Vertical value; LLK |
8.88 | PE | Nelsen and Buschek, 1974 | Vertical value; LLK |
8.88 | PE | Nelsen and Buschek, 1974, 2 | Vertical value; LLK |
Appearance energy determinations
References
Go To: Top, Phase change data, 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.
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]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
McMillan, 1967
McMillan, J.A.,
Hydrazine-1,1-Dimethylhydrazine Solid-Liquid Phase Diagram,
J. Chem. Eng. Data, 1967, 12, 39. [all data]
Aston, Wood, et al., 1953
Aston, J.G.; Wood, J.L.; Zolki, T.P.,
The Thermodynamic Properties and Configuration of Unsymmetrical Dimethylhydrazine,
J. Am. Chem. Soc., 1953, 75, 6202. [all data]
Aston, Wood, et al., 1953, 2
Aston, J.G.; Wood, J.L.; Zolki, T.P.,
The thermodynamic properties and configuration of unsymmetrical dimethylhydrazine,
J. Am. Chem. Soc., 1953, 75, 6202-62. [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]
Aston, Wood, et al., 1953, 3
Aston, J.G.; Wood, J.L.; Zolki, T.P.,
The thermodynamic properties and configuration of unsymmetrical dimethylhydrazine,
J. Am. Chem. Soc., 1953, 75, 6202-6204. [all data]
Bourret-Courchesne, Ye, et al., 2000
Bourret-Courchesne, E.; Ye, Q.; Peters, D.W.; Arnold, J.; Ahmed, M.; Irvine, S.J.C.; Kanjolia, R.; Smith, L.M.; Rushworth, S.A.,
Pyrolysis of dimethylhydrazine and its co-pyrolysis with triethylgallium,
Journal of Crystal Growth, 2000, 217, 1-2, 47-54, https://doi.org/10.1016/S0022-0248(00)00398-5
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Mautner(Meot-Ner), Nelsen, et al., 1984
Mautner(Meot-Ner), M.; Nelsen, S.F.; Willi, M.R.; Frigo, T.B.,
Special effects of an unusually large neutral to radical cation geometry change. Adiabatic ionization energies and proton affinities of alkylhydrazines,
J. Am. Chem. Soc., 1984, 106, 7384. [all data]
Vovna, Vilesov, et al., 1975
Vovna, V.I.; Vilesov, F.I.; Lopatin, S.N.,
Photoelectron spectra of hydrazine and some alkyl derivatives,
Opt. Spectrosc., 1975, 38, 143. [all data]
Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Jennings, W.B.; Worley, S.D.,
Photoelectron spectra of molecules-IV.Ionization potentials and heats of formation of some hydrazines and amines,
Tetrahedron, 1970, 26, 4109. [all data]
Akopyan and Vilesov, 1963
Akopyan, M.E.; Vilesov, F.I.,
Decay of the molecular ions formed in photoionization of hydrazine and some of its alkyl derivatives,
Kinetika i Kataliz, 1963, 4, 39, In original 32. [all data]
Akopyan, Vilesov, et al., 1963
Akopyan, M.E.; Vilesov, F.I.; Terenin, A.N.,
Mass spectrometric investigation of photoionization of molecules and dissociation of excited molecular ions,
Izv. Akad. Nauk SSSR, Ser. Fiz., 1963, 27, 1083, In original 1054. [all data]
Dibeler, Franklin, et al., 1959
Dibeler, V.H.; Franklin, J.L.; Reese, R.M.,
Electron impact studies of hydrazine and the methyl-substituted hydrazines,
J. Am. Chem. Soc., 1959, 81, 68. [all data]
Rademacher, 1975
Rademacher, P.,
Acyclische Hydrazine,
Chem. Ber., 1975, 108, 1548. [all data]
Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Osafune, K.,
Photoelectron spectroscopic study of skew compounds. Methylhydrazine and unsymmetrical dimethylhydrazine,
Bull. Chem. Soc. Jpn., 1975, 48, 2736. [all data]
Nelsen and Buschek, 1974
Nelsen, S.F.; Buschek, J.M.,
Photoelectron spectra of hydrazines. IV. Empirical estimation of lone pair-lone pair dihedral angles and prediction of lone pair ionization potentials for some cyclic and bicyclic hydrazines,
J. Am. Chem. Soc., 1974, 96, 6982. [all data]
Nelsen and Buschek, 1974, 2
Nelsen, S.F.; Buschek, J.M.,
Photoelectron spectra of hydrazines. III. Evidence for similar lone pair-lone pair dihedral angles for acyclic hydrazines,
J. Am. Chem. Soc., 1974, 96, 2392. [all data]
Burgers, Drewello, et al., 1989
Burgers, P.C.; Drewello, T.; Schwarz, H.; Terlouw, J.K.,
CH5N2 hydrazyl radicals, cations and dication radicals studied by mass spectrometry. Is the N-protonated formaldehyde hydrazon cation +CH2-NH-NH2 a bridged species?,
Int. J. Mass Spectrom. Ion Processes, 1989, 95, 157. [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]
Foner and Hudson, 1970
Foner, S.N.; Hudson, R.L.,
Mass spectrometric studies of atom-molecule reactions using high-intensity crossed molecular beams,
J. Chem. Phys., 1970, 53, 4377. [all data]
Foner and Hudson, 1962
Foner, S.N.; Hudson, R.L.,
Mass spectrometry of inorganic free radicals,
Advan. Chem. Ser., 1962, 36, 34. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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