Tetramethylhydrazine

• Formula: C₄H₁₂N₂
• Molecular weight: 88.1515
• IUPAC Standard InChI: InChI=1S/C4H12N2/c1-5(2)6(3)4/h1-4H3 Copy

  
• IUPAC Standard InChIKey: DHBZRQXIRAEMRO-UHFFFAOYSA-N Copy
• CAS Registry Number: 6415-12-9
• 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: (CH3)2NN(CH3)2; Hydrazine, tetramethyl-
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• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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: William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Reaction 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₄H₁₂N₂⁺ +  = (C₄H₁₂N₂⁺ • )

By formula: C₄H₁₂N₂⁺ + C₄H₁₂N₂ = (C₄H₁₂N₂⁺ • C₄H₁₂N₂)

Bond type: Charge transfer bond (positive ion)

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:
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

Ionization energy determinations

Appearance energy determinations

Ion clustering 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Clustering reactions

C₄H₁₂N₂⁺ +  = (C₄H₁₂N₂⁺ • )

By formula: C₄H₁₂N₂⁺ + C₄H₁₂N₂ = (C₄H₁₂N₂⁺ • C₄H₁₂N₂)

Bond type: Charge transfer bond (positive ion)

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

Gas Phase Spectrum

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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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

Gas Chromatography

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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

Normal alkane RI, non-polar column, temperature ramp

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References

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

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]

Hickinbottom, Rogers, et al., 1957
Hickinbottom, W.J.; Rogers, N.W.; Clark, H.C.; Cox, B.; Sharpe, A.G.; Barakat, M.Z.; Shehab, S.K.; El-Sadr, M.M.; Pauncz, R.; Aynsley, E.E.; Campbell, W.A.; Baddiley, J.; Buchanan, J.G.; Carss, B.; Woodcock, D.; Clifford, D.R.; Faseeh, S.A.; Harley-Mason, John; Merchant, J.R.; Naik, R.M.; Mountwalla, A.J.; Williams, R.L.; Pace, R.J.; O'Sullivan, D.G.; Sadler, P.W.; Cocker, Wesley; Cross, B.E.; Williamson, W.R.N.; Mcilroy, R.J.; Everest, D.A.; Bird, C.W.; Norymberski, J.K.; Woods, Gilbert F.; Heath, D.F.; Aylett, B.J.; Cadogan, J.I.G.; Johnson, E.A., Notes, J. Chem. Soc., 1957, 4131, https://doi.org/10.1039/jr9570004131 . [all data]

Nelsen, Rumak, et al., 1987
Nelsen, S.F.; Rumak, D.T.; Meot-Ner (Mautner), M., Kinetic effects of an unusually large neutral to radical cation geometry change. Slow electron transfer rections between alkylhydrazines, J. Am. Chem. Soc., 1987, 109, 5, 1373, https://doi.org/10.1021/ja00239a015 . [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]

Rumack, 1986
Rumack, D., Title unavailable, Personal communication to S.G. Lias, 1986. [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]

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]

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]

Nelsen, 1984
Nelsen, S.F., Ionization from nitrogen and oxygen lone pairs: A comparison of trialkylamine, dialkyl ether, tetraalkylhydrazine, and dialkyl peroxide photoelectron spectroscopic ionization potentials, J. Org. Chem., 1984, 49, 1891. [all data]

Bock, Kaim, et al., 1980
Bock, H.; Kaim, W.; Noth, H.; Semkow, A., A radical ions. 36. Structural changes accompanying the one-electron oxidation of hydrazine and its silyl derivatives, J. Am. Chem. Soc., 1980, 102, 4421. [all data]

Nelsen, Peacock, et al., 1976
Nelsen, S.F.; Peacock, V.; Weisman, G.R., Single-electron oxidation equilibria of tetraalkylhydrazines. Comparison of solution E° values and vapor-phase ionization potentials, J. Am. Chem. Soc., 1976, 98, 5269. [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]

Rademacher, 1973
Rademacher, P., Photoelectron spectra and conformation of hydrazine derivatives, Angew. Chem. Int. Ed. Engl., 1973, 12, 408. [all data]

Nelsen and Buschek, 1973
Nelsen, S.F.; Buschek, J.M., Photoelectron spectra of hydrazines. I. Dependence of the lone pair-lone pair splitting on dihedral angle for tetraalkylhydrazines, J. Am. Chem. Soc., 1973, 95, 2011. [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]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

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