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
  The 3d structure may be viewed using Java or Javascript.
• 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)
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

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

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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.

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]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References

• 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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