Urea

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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:
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

Quantity Value Units Method Reference Comment
Tfus406. ± 3.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple407.9KN/AFerloni and DellaGatta, 1995Uncertainty assigned by TRC = 0.2 K; TRC
Ttriple408.KN/AKabo, Miroshnichenko, et al., 1990Uncertainty assigned by TRC = 0.00001 K; TRC
Ttriple405.8KN/AKozyro, Dalidovich, et al., 1986Uncertainty assigned by TRC = 0.1 K; TRC
Ttriple405.8KN/AVogel and Schuberth, 1980Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δsub22.8 ± 0.07kcal/molGSEmel'yanenko, Kabo, et al., 2006Based on data from 358. to 402. K.; AC
Δsub23.6kcal/molN/ADe Wit, Van Miltenburg, et al., 1983AC
Δsub20.95 ± 0.21kcal/molVSuzuki, Onishi, et al., 1956ALS

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
22.6 ± 0.53370.MEZaitsau, Kabo, et al., 2003Based on data from 329. to 403. K.; AC
22.7 ± 0.53350.MEZaitsau, Kabo, et al., 2003Based on data from 329. to 403. K.; AC
22.6 ± 0.1350.CZaitsau, Kabo, et al., 2003AC
23.3 ± 0.24354.CKabo, Miroshnichenko, et al., 1990, 2see Simirsky, Kabo, et al., 1987; ALS
21.7381.N/AFerro, Barone, et al., 1987AC
21.0357.N/AStephenson and Malanowski, 1987Based on data from 345. to 368. K.; AC
23.2351.TE,MEDe Wit, Van Miltenburg, et al., 1983Based on data from 338. to 362. K.; AC
22.8361.N/ATrimble and Voorhoeve, 1978AC
21.0 ± 0.50356.N/ASuzuki, Onishi, et al., 1956, 2Based on data from 345. to 368. K. See also Jones, 1960 and Cox and Pilcher, 1970.; AC
21.1357.N/ABradley and Cleasby, 1953See also De Wit, Van Miltenburg, et al., 1983.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
3.5349406.5N/ADella Gatta and Ferro, 1987DH
3.3222405.8N/AKozyro, Dalidovich, et al., 1986, 2DH
3.4656406.N/AGambino and Bros, 1988DH
3.2529405.8N/AVogel and Schuberth, 1980, 2DH
3.49407.2DSCRai and Rai, 1999AC
3.25405.2DSCJamróz, Palczewska-Tulinska, et al., 1998AC
3.49406.7DSCRai and Rai, 1998AC
3.592407.9DSCFerloni and Gatta, 1995AC
3.090408.1N/AKabo, Miroshnichenko, et al., 1990, 2AC
3.32405.8N/AKozyro, Dalidovich, et al., 1986AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
8.70406.5Della Gatta and Ferro, 1987DH
8.186405.8Kozyro, Dalidovich, et al., 1986, 2DH
8.53406.Gambino and Bros, 1988DH
8.016405.8Vogel and Schuberth, 1980, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 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

Proton affinity (kcal/mol) Reference Comment
207.6 ± 0.60Zheng and Cooks, 2002MM
208.8 ± 1.2Wang, Ma, et al., 1998m-bromoaniline; p-fluorobenzamide; MM
208.8 ± 1.2Wang, Ma, et al., 1998T = T(eff) = 410-560 KK; Acrylamide;m-Bromoaniline; MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
200.5 ± 0.72Zheng and Cooks, 2002MM
202.2 ± 1.2Wang, Ma, et al., 1998m-bromoaniline; p-fluorobenzamide; MM
201.1 ± 1.2Wang, Ma, et al., 1998T = T(eff) = 410-560 KK; Acrylamide;m-Bromoaniline; MM

Protonation entropy at 298K

Protonation entropy (cal/mol*K) Reference Comment
2.2Zheng and Cooks, 2002MM
-0.45Wang, Ma, et al., 1998T = T(eff) = 410-560 KK; Acrylamide;m-Bromoaniline; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.7PEDebies and Rabalais, 1974LLK
10.27 ± 0.05EIBaldwin, Kirkien-Konasiewicz, et al., 1966RDSH
9.8PEBieri, Asbrink, et al., 1982Vertical value; LBLHLM
10.28PEDougherty, Wittel, et al., 1976Vertical value; LLK
10.33PEMines and Thompson, 1975Vertical value; LLK
10.15PEMeeks, Arnett, et al., 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2NO+12.90?EILoudon and Webb, 1977LLK

De-protonation reactions

CH3N2O- + Hydrogen cation = Urea

By formula: CH3N2O- + H+ = CH4N2O

Quantity Value Units Method Reference Comment
Δr361.8 ± 2.8kcal/molCIDCMa, Wang, et al., 1998gas phase; H and S (20.5±1.8 eu) directly from kinetic method; B
Δr362.5 ± 2.6kcal/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale; B
Δr357.4 ± 2.1kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr355.7 ± 3.2kcal/molH-TSMa, Wang, et al., 1998gas phase; H and S (20.5±1.8 eu) directly from kinetic method; B
Δr355.5 ± 2.5kcal/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale; B

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.

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]

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]

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]


Notes

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