Urea, tetramethyl-

• Formula: C₅H₁₂N₂O
• Molecular weight: 116.1616
• IUPAC Standard InChI: InChI=1S/C5H12N2O/c1-6(2)5(8)7(3)4/h1-4H3 Copy

  
• IUPAC Standard InChIKey: AVQQQNCBBIEMEU-UHFFFAOYSA-N Copy
• CAS Registry Number: 632-22-4
• 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: Temur; Tetramethylurea; ((CH3)2N)2CO; 1,1,3,3-Tetramethylurea; TMU; Urea, 1,1,3,3-tetramethyl-; Tetramethyluree; N,N,N',N'-Tetramethylurea; NSC 91488; Urea, N,N,N',N'-tetramethyl-
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• 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 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

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

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

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]

Kozyro, Krasulin, et al., 1988
Kozyro, A.A.; Krasulin, A.P.; Simirsky, V.V.; Markovnik, V.S., Thermodynamic properties of tetramethylurea, Zh. Fiz. Khim., 1988, 62, 1747-52. [all data]

Zordan, Hurkot, et al., 1972
Zordan, T.A.; Hurkot, D.G.; Peterson, M.; Hepler, L.G., Enthalpies and entropies of melting from differential scanning calorimetry and freezing point depressions: urea, methylurea, 1, 1-dimethylurea, 1, 3- dimethylurea, tetramethylurea, and thiourea, Thermochim. Acta, 1972, 5, 21. [all data]

Kabo, Kozyro, et al., 1995
Kabo, G.Ya.; Kozyro, A.A.; Diky, V.V.; Simirsky, V.V., Additivity of Thermodynamic Properties of Organic Compounds in Crystalline State. 2. Heat Capacities and Enthalpies of Phase Transition of Alkyl Derivatives of Urea in Crystalline State, J. Chem. Eng. Data, 1995, 40, 371-93. [all data]

Kabo, Miroshnichenko, et al., 1990
Kabo, G.Ya.; Miroshnichenko, E.A.; Frenkel, M.L.; Kozyro, A.A.; Simirskii, V.V.; Krasulin, A.P.; Vorob'eva, V.P.; Lebedev, Yu.A., Thermochemistry of urea alkyl derivatives, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 662-667. [all data]

Simirsky, Kabo, et al., 1987
Simirsky, V.V.; Kabo, G.J.; Frenkel, M.L., Additivity of the enthalpies of formation of urea derivatives in the crystalline state, J. Chem. Thermodyn., 1987, 19, 1121-1127. [all data]

Kozyro, Krasulin, et al., 1988, 2
Kozyro, A.A.; Krasulin, A.P.; Simirskii, V.V.; Markovnik, V.S., Thermodynamic properties of tetramethylurea, Russ. J. Phys. Chem. (Engl. Transl.), 1988, 62, 895-897. [all data]

Kneisl and Zondlo, 1987
Kneisl, Philip; Zondlo, John W., Vapor pressure, liquid density, and the latent heat of vaporization as functions of temperature for four dipolar aprotic solvents, J. Chem. Eng. Data, 1987, 32, 1, 11-13, https://doi.org/10.1021/je00047a003 . [all data]

Kozyro, Krasulin, et al., 1988, 3
Kozyro, A.A.; Krasulin, A.P.; Simirskii, V.V.; Markovnik, V.S., Thermodynamic properties of tetramethylurea, Zhur. Fiz. Khim., 1988, 62, 1747-1751. [all data]

Jamróz, Dobrowolski, et al., 2001
Jamróz, Malgorzata E.; Dobrowolski, Jan Cz.; Polaczek, Jerzy; Szafranski, Andrzej M.; Kazimirski, Jan K.; Lisicki, Zygmunt, (Solid + liquid) equilibria, i.r., and semi-empirical studies of carbazole with selected tertiary amides, The Journal of Chemical Thermodynamics, 2001, 33, 5, 565-579, https://doi.org/10.1006/jcht.2000.0770 . [all data]

Kabo, Kozyro, et al., 1995, 2
Kabo, Gennady J.; Kozyro, Alexander A.; Diky, Vladimir V.; Simirsky, Vladimir V., Additivity of Thermodynamic Properties of Organic Compounds in Crystalline State. 2. Heat Capacities and Enthalpies of Phase Transition of Alkyl Derivatives of Urea in Crystalline State, J. Chem. Eng. Data, 1995, 40, 2, 371-393, https://doi.org/10.1021/je00018a005 . [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]

Baldwin, Kirkien-Konasiewicz, et al., 1966
Baldwin, M.; Kirkien-Konasiewicz, A.; Loudon, A.G.; Maccoll, A.; Smith, D., Localised or delocalised charges in molecule-ions?, Chem. Commun., 1966, 574. [all data]

Dougherty, Wittel, et al., 1976
Dougherty, D.; Wittel, K.; Meeks, J.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. Ureas, uracils, and thymine, J. Am. Chem. Soc., 1976, 98, 3815. [all data]

Mines and Thompson, 1975
Mines, G.W.; Thompson, H.W., The photoelectron spectra of amides, thioamides, ureas and thioureas, Spectrochim. Acta, 1975, 31, 137. [all data]

Loudon and Webb, 1977
Loudon, A.G.; Webb, K.S., The nature of the [C₂H₆N]⁺ and [CH₄N]⁺ ions formed by electron impact on methylated formamides, acetamides, ureas, thioureas and hexamethylphosphoramide, Org. Mass Spectrom., 1977, 12, 283. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance 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

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