Carbonic acid, dimethyl ester

• Formula: C₃H₆O₃
• Molecular weight: 90.0779
• IUPAC Standard InChI: InChI=1S/C3H6O3/c1-5-3(4)6-2/h1-2H3 Copy

  
• IUPAC Standard InChIKey: IEJIGPNLZYLLBP-UHFFFAOYSA-N Copy
• CAS Registry Number: 616-38-6
• 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: Dimethyl carbonate; Methyl carbonate; Methyl carbonate ((MeO)2CO); CH3OCOOCH3; UN 1161; Dimethyl ester of carbonic acid
• 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:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

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
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Enthalpy 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
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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.

Biltz, Fischer, et al., 1930
Biltz, W.; Fischer, W.; Wunnenberg, E., Molecular and Atomic Volumes. The Volume Requirements of Crystalline Organic Compounds and Low Temperatures, Z. Phys. Chem., Abt. A, 1930, 151, 13-55. [all data]

Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturated Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Trimethyl benzene, Pentafluorophenol, 4-tert-Butylcatechol, .alp, J. Chem. Eng. Data, 1997, 42, 1008-20. [all data]

Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermocynamic Properties and Ideal-Gas Enthalpies of Formation for Carbonate, Piperazine, Hexachloroprop-1-ene, Tetrakis(dimethylamino) ethylene, N,N'-Bis(2-hydroxyethyl)ethylenediamine, and 1,2,4-Tr, J. Chem. Eng. Data, 1997, 42, 1037-52. [all data]

Kozlova, Emel'yanenko, et al., 2008
Kozlova, Svetlana A.; Emel'yanenko, Vladimir N.; Georgieva, Miglena; Verevkin, Sergey P.; Chernyak, Yury; Schäffner, Benjamin; Börner, Armin, Vapour pressure and enthalpy of vaporization of aliphatic dialkyl carbonates, The Journal of Chemical Thermodynamics, 2008, 40, 7, 1136-1140, https://doi.org/10.1016/j.jct.2008.02.012 . [all data]

Steele, Chirico, et al., 1997, 3
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Dicyclohexyl Sulfide, Diethylenetriamine, Di- n -octyl Sulfide, Dimethyl Carbonate, Piperazine, Hexachloroprop-1-ene, Tetrakis(dimethylamino)ethylene, N , N '-Bis-(2-hydroxyethyl)ethylenediamine, and 1,2,4-Triazolo[1,5- a ]pyrimidine, J. Chem. Eng. Data, 1997, 42, 6, 1037-1052, https://doi.org/10.1021/je9700986 . [all data]

Steele, Chirico, et al., 1997, 4
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Triethylbenzene, Pentafluorophenol, 4- tert -Butylcatechol, α-Methylstyrene, and N , N '-Bis(2-hydroxyethyl)ethylenediamine, J. Chem. Eng. Data, 1997, 42, 6, 1008-1020, https://doi.org/10.1021/je970102d . [all data]

Rodriguez, Canosa, et al., 2002
Rodriguez, A.; Canosa, J.; Dominguez, A.; Tojo, J., Isobaric vapour--liquid equilibria of dimethyl carbonate with alkanes and cyclohexane at 101.3 kPa, Fluid Phase Equilibria, 2002, 198, 1, 95-109, https://doi.org/10.1016/S0378-3812(01)00761-0 . [all data]

Ding, 2004
Ding, Michael S., Liquid-Solid Phase Equilibria and Thermodynamic Modeling for Binary Organic Carbonates, J. Chem. Eng. Data, 2004, 49, 2, 276-282, https://doi.org/10.1021/je034134e . [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]

McGlynn and Meeks, 1976
McGlynn, S.P.; Meeks, J.L., Photoelectron spectra of carbonyls, carbonates, oxalates and esterification effects, J. Electron Spectrosc. Relat. Phenom., 1976, 8, 85. [all data]

Wittel, Astrup, et al., 1975
Wittel, K.; Astrup, E.E.; Bock, H.; Graeffe, G.; Juslen, H., Photoelectron spectra and molecular properties, XLVIII Carbonates thio- carbonates, Z. Naturforsch. B:, 1975, 30, 862. [all data]

Meeks, Arnett, et al., 1975
Meeks, J.L.; Arnett, J.F.; Larson, D.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. Ionization assignments, Chem. Phys. Lett., 1975, 30, 190. [all data]

Suh, Kingsmill, et al., 1995
Suh, D.; Kingsmill, C.A.; Ruttink, P.J.A.; Burgers, P.C.; Terlouw, J.K., C-H...O and O...H...O bonded intermediates in the dissociation of low energy methyl glycolate radical cations, Int. J. Mass Spectrom. Ion Processes, 1995, 146/147, 305. [all data]

Blanchette, Holmes, et al., 1986
Blanchette, M.C.; Holmes, J.L.; Hop, C.E.C.A.; Lossing, F.P.; Postma, R.; Ruttink, P.J.A.; Terlouw, J.K., Theory and experiment in concert; the CH₃O-C=O⁺ ion and its isomers, J. Am. Chem. Soc., 1986, 108, 7589. [all data]

Briggs and Shannon, 1969
Briggs, P.R.; Shannon, T.W., The heat of formation of the methoxycarbonyl ion, J. Am. Chem. Soc., 1969, 91, 4307. [all data]

Terlouw, Wezenberg, et al., 1983
Terlouw, J.K.; Wezenberg, J.; Burgers, P.C.; Holmes, J.L., New stable isomers of [C₂H₄O]⁺ and [C₂H₄O₂]⁺, the radical cations [CH₂COH]⁺ and [CH₃OCOH]⁺, J. Chem. Soc., Chem. Commun., 1983, 1121. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.