Urea

• Formula: CH₄N₂O
• Molecular weight: 60.0553
• IUPAC Standard InChI: InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4) Copy

  
• IUPAC Standard InChIKey: XSQUKJJJFZCRTK-UHFFFAOYSA-N Copy
• CAS Registry Number: 57-13-6
• 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: Carbamide; Carbamimidic acid; Carbonyldiamide; Isourea; Pseudourea; Urea-13C; Ureaphil; Ureophil; Urevert; UR; (NH2)2CO; Carbonyl Diamine; Alphadrate; Aquacare; Aquadrate; B-I-K; Calmurid; Carbaderm; Keratinamin; NCI-C02119; Pastaron; Prespersion, 75 urea; Ultra Mide; Urepearl; Mocovina; Supercel 3000; Varioform II; Benural 70; Harnstoff; Basodexan; Bubber shet; Elaqua xx; Hyanit; Nutraplus; Onychomal; NSC 34375; Uroderm; Panafil (Salt/Mix); Cerovel (Salt/Mix); component of Artra Ashy Skin Cream (Salt/Mix)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry 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:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

Go To: Top, Phase change data, 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

CH₃N₂O^- +  =

By formula: CH₃N₂O^- + H⁺ = CH₄N₂O

 +  =

By formula: CH₄N₂O + C₄H₄O₂ = N-(aminocarbonyl)-3-oxobutyramide

6 =  + 3 + 6

By formula: 6CH₄N₂O = C₃H₆N₆ + 3CO₂ + 6H₃N

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry 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:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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

Proton affinity at 298K

Gas basicity at 298K

Protonation entropy at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

CH₃N₂O^- +  =

By formula: CH₃N₂O^- + H⁺ = CH₄N₂O

References

Go To: Top, Phase change data, Reaction thermochemistry 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.

Ferloni and DellaGatta, 1995
Ferloni, P.; DellaGatta, G., Heat capacities of urea, N-methylurea, N-ethylurea, N-(n)propylurea, and N- (n)butylurea in the range 200 to 360 K, Thermochim. Acta, 1995, 266, 203-12. [all data]

Kabo, Miroshnichenko, et al., 1990
Kabo, G.Ya.; Miroshnichenko, E.A.; Frenkel, M.L.; Kozyro, A.A.; Simirsky, V.V.; Krasulin, A.P.; Vorob'eva, V.P.; Lebedev, Yu.A., Thermochemistry of Alkyl Derivatives of Urea, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, No. 4, 750-5. [all data]

Kozyro, Dalidovich, et al., 1986
Kozyro, A.A.; Dalidovich, S.V.; Krausulin, A.P., Zh. Prikl. Khim. (S.-Peterburg), 1986, 59, 1456. [all data]

Vogel and Schuberth, 1980
Vogel, L.; Schuberth, H., Some physicochemical data of urea near the melting point<, Chem. Tech. (Leipzig), 1980, 32, 143. [all data]

Emel'yanenko, Kabo, et al., 2006
Emel'yanenko, Vladimir N.; Kabo, Gennady J.; Verevkin, Sergey P., Measurement and Prediction of Thermochemical Properties: Improved Increments for the Estimation of Enthalpies of Sublimation and Standard Enthalpies of Formation of Alkyl Derivatives of Urea, J. Chem. Eng. Data, 2006, 51, 1, 79-87, https://doi.org/10.1021/je050230z . [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

Suzuki, Onishi, et al., 1956
Suzuki, K.; Onishi, S.; Koide, T.; Seki, S., Vapor pressures of molecular crystals. XI. Vapor pressures of crystalline urea and diformylhydrazine. Energies of hydrogen bonds in these crystals, Bull. Chem. Soc. Jpn., 1956, 29, 127. [all data]

Zaitsau, Kabo, et al., 2003
Zaitsau, Dz; Kabo, G.J.; Kozyro, A.A.; Sevruk, V.M., The effect of the failure of isotropy of a gas in an effusion cell on the vapor pressure and enthalpy of sublimation for alkyl derivatives of carbamide, Thermochimica Acta, 2003, 406, 1-2, 17-28, https://doi.org/10.1016/S0040-6031(03)00231-4 . [all data]

Kabo, Miroshnichenko, et al., 1990, 2
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]

Ferro, Barone, et al., 1987
Ferro, D.; Barone, G.; Della Gatta, G.; Piacente, V., Vapour pressures and sublimation enthalpies of urea and some of its derivatives, The Journal of Chemical Thermodynamics, 1987, 19, 9, 915-923, https://doi.org/10.1016/0021-9614(87)90038-3 . [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]

Trimble and Voorhoeve, 1978
Trimble, L.E.; Voorhoeve, R.J.H., Continuous colorimetric monitoring of vapour-phase urea and cyanates, Analyst, 1978, 103, 1228, 759, https://doi.org/10.1039/an9780300759 . [all data]

Suzuki, Onishi, et al., 1956, 2
Suzuki, Keisuke; Onishi, Shun-ichi; Koide, Tsutomu; Seki, Syuzo, Vapor Pressures of Molecular Crystals. XI. Vapor Pressures of Crystalline Urea and Diformylhydrazine. Energies of Hydrogen Bonds in these Crystals, Bull. Chem. Soc. Jpn., 1956, 29, 1, 127-131, https://doi.org/10.1246/bcsj.29.127 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Bradley and Cleasby, 1953
Bradley, R.S.; Cleasby, T.G., 346. The vapour pressure and lattice energy of hydrogen-bonded crystals. Part I. Oxamide, oxamic acid, and rubeanic acid, J. Chem. Soc., 1953, 1681, https://doi.org/10.1039/jr9530001681 . [all data]

Della Gatta and Ferro, 1987
Della Gatta, G.; Ferro, D., Enthalpies of fusion and solid-to-solid transition, entropies of fusion for urea and twelve alkylureas, Thermochim. Acta, 1987, 122, 143-152. [all data]

Kozyro, Dalidovich, et al., 1986, 2
Kozyro, A.A.; Dalidovich, S.V.; Krasulin, A.P., Heat capacity, enthalpy of fusion, and thermodynamic properties of urea, Zhur. Prikl. Khim. (Leningrad), 1986, 59, 1456-1459. [all data]

Gambino and Bros, 1988
Gambino, M.; Bros, J.P., Capacite calorifique de l'uree et de quelques melanges eutectiques a base d'uree entre 30 et 140°C, Thermochim. Acta, 1988, 127, 223-236. [all data]

Vogel and Schuberth, 1980, 2
Vogel, L.; Schuberth, H., Some physicochemical data of urea near the melting point, Chem. Tech. (Leipzig), 1980, 32, 143-144. [all data]

Rai and Rai, 1999
Rai, U.S.; Rai, R.N., Some Physicochemical Studies on Organic Eutectics and Molecular Complex: Urea -- p-nitrophenol System, J. Mater. Res., 1999, 14, 04, 1299-1305, https://doi.org/10.1557/JMR.1999.0177 . [all data]

Jamróz, Palczewska-Tulinska, et al., 1998
Jamróz, Malgorzata E.; Palczewska-Tulinska, Marcela; Wyrzykowska-Stankiewicz, Danuta; Szafranski, Andrzej M.; Polaczek, Jerzy; Dobrowolski, Jan Cz.; Jamróz, Michal H.; Mazurek, Aleksander P., The urea--phenol(s) systems, Fluid Phase Equilibria, 1998, 152, 2, 307-326, https://doi.org/10.1016/S0378-3812(98)90206-0 . [all data]

Rai and Rai, 1998
Rai, U.S.; Rai, R.N., Journal of Thermal Analysis and Calorimetry, 1998, 53, 3, 883-893, https://doi.org/10.1023/A:1010190402954 . [all data]

Ferloni and Gatta, 1995
Ferloni, Paolo; Gatta, Giuseppe Della, Heat capacities of urea, N-methylurea, N-ethylurea, N-(n)propylurea, and N-(n)butylurea in the range 200 to 360 K, Thermochimica Acta, 1995, 266, 203-212, https://doi.org/10.1016/0040-6031(95)02453-0 . [all data]

Ma, Wang, et al., 1998
Ma, S.G.; Wang, F.; Cooks, R.G., Gas-phase acidity of urea, J. Mass Spectrom., 1998, 33, 10, 943-949, https://doi.org/10.1002/(SICI)1096-9888(1998100)33:10<943::AID-JMS703>3.0.CO;2-B . [all data]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A., Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry, Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C . [all data]

Lopatin, Popov, et al., 1992
Lopatin, E.B.; Popov, V.V.; Epshtein, N.A.; Mikhaleva, L.M.; Makarov, Yu.N., Kinetic and thermochemical characteristics of diketene-based reactions, Khim.-Farm. Zh., 1992, 26, 76-78. [all data]

Rukevich and Zagranichnyi, 1971
Rukevich, O.S.; Zagranichnyi, V.I., Equilibrium in the reaction of melamine formation from urea, J. Anal. Chem. USSR, 1971, 44, 1616-1620. [all data]

Zheng and Cooks, 2002
Zheng, X.; Cooks, R.G., Thermochemical determinations by the kinetic method with direct entropy corrrection, J. Phys. Chem. A, 2002, 106, 9939. [all data]

Wang, Ma, et al., 1998
Wang, F.; Ma, S.G.; Zhang, D.X.; Cooks, R.G., Proton affinity and gas-phase basicity of urea, J. Phys. Chem. A., 1998, 102, 2988. [all data]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Electronic structure of amino acids and ureas, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 315. [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]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [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]

Meeks, Arnett, et al., 1975
Meeks, J.L.; Arnett, J.F.; Larson, D.B.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. Urea, oxamide, oxalic acid and oxamic acid, J. Am. Chem. Soc., 1975, 97, 3905. [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

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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