Urea, N,N-dimethyl-
- Formula: C3H8N2O
- Molecular weight: 88.1084
- IUPAC Standard InChIKey: YBBLOADPFWKNGS-UHFFFAOYSA-N
- CAS Registry Number: 598-94-7
- 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: Urea, 1,1-dimethyl-; Asym-Dimethylurea; N,N-Dimethylurea; 1,1-Dimethylurea; (CH3)2NCONH2
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -52.57 ± 0.27 | kcal/mol | Ccb | Kabo, Miroshnichenko, et al., 1990 | see Simirsky, Kabo, et al., 1987 |
Condensed phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -76.26 ± 0.16 | kcal/mol | Ccb | Kabo, Miroshnichenko, et al., 1990 | see Simirsky, Kabo, et al., 1987 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -479.16 ± 0.13 | kcal/mol | Ccb | Kabo, Miroshnichenko, et al., 1990 | see Simirsky, Kabo, et al., 1987 |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 |
---|---|---|---|---|---|
Tfus | 454. | K | N/A | DellaGatta and Ferro, 1987 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 455.2 | K | N/A | Zordan, Hurkot, et al., 1972 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22.3 ± 0.07 | kcal/mol | GS | Emel'yanenko, Kabo, et al., 2006 | Based on data from 346. to 398. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.6 ± 0.33 | 348. | ME | Zaitsau, Kabo, et al., 2003 | Based on data from 323. to 372. K.; AC |
22.6 ± 0.33 | 350. | ME | Zaitsau, Kabo, et al., 2003 | Based on data from 323. to 372. K.; AC |
22.3 ± 0.1 | 350. | C | Zaitsau, Kabo, et al., 2003 | AC |
23.7 ± 0.2 | 353. | C | Kabo, Miroshnichenko, et al., 1990 | see Simirsky, Kabo, et al., 1987; ALS |
22.1 ± 0.31 | 357. | TE | Piacente, Ferro, et al., 1990 | Based on data from 326. to 369. K. See also Ferro, Barone, et al., 1987.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.0770 | 454.0 | Della Gatta and Ferro, 1987 | DH |
6.957 | 454. | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.6 | 454.0 | Della Gatta and Ferro, 1987 | DH |
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 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
C3H7N2O- + =
By formula: C3H7N2O- + H+ = C3H8N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 361.8 ± 2.5 | kcal/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 354.8 ± 2.4 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: CH2O + C3H8N2O = C4H10N2O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.8 ± 0.2 | kcal/mol | Kin | Perepelkova, Igranova, et al., 1981 | liquid phase; solvent: Phosphate buffer; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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
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
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.10 ± 0.05 | EI | Baldwin, Kirkien-Konasiewicz, et al., 1966 | RDSH |
8.96 | PE | Dougherty, Wittel, et al., 1976 | Vertical value; LLK |
De-protonation reactions
C3H7N2O- + =
By formula: C3H7N2O- + H+ = C3H8N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 361.8 ± 2.5 | kcal/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 354.8 ± 2.4 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-5005 |
NIST MS number | 230091 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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.
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]
DellaGatta and Ferro, 1987
DellaGatta, G.; Ferro, D.,
Enthalpies of fusion and solid-to-solid transition, entropies of fusion for urea and twelve alkylurea,
Thermochim. Acta, 1987, 122, 143-52. [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]
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]
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]
Piacente, Ferro, et al., 1990
Piacente, V.; Ferro, D.; Gatta, G. Della,
Sublimation enthalpy of eleven alkyl derivatives of urea,
Thermochimica Acta, 1990, 158, 1, 79-85, https://doi.org/10.1016/0040-6031(90)80054-3
. [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]
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]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
Perepelkova, Igranova, et al., 1981
Perepelkova, T.I.; Igranova, E.G.; Moiseev, V.D.; Demchenko, L.Ya.; Zhuravleva, I.I.,
Calorimetric study of the methylolation of 1,1-dimethylurea,
Khim. Promst. Ser. Proizvod. Pererab. Plastmass Sint. Smol, 1981, 15-18. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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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