Diethyl malonate

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Gas 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-190.1kcal/molSemiStewart, 2004 
Δfgas-220.3 ± 1.0kcal/molCcbVerevkin, Beckhaus, et al., 1992Hc value was corrected by private communication with authors; ALS

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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil472.5KN/AWeast and Grasselli, 1989BS
Tboil373.35KN/ALecat, 1943Uncertainty assigned by TRC = 0.4 K; TRC
Tboil472.05KN/ATimmermans, 1911Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tfus221.7KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.5 K; TRC
Tfus224.3KN/APalomaa and Mikkila, 1942Uncertainty assigned by TRC = 1. K; TRC
Tfus223.25KN/ATimmermans, 1911Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Δvap15.46 ± 0.05kcal/molVVerevkin, Beckhaus, et al., 1992Hc value was corrected by private communication with authors; ALS
Δvap15.5kcal/molN/AVerevkin, Beckhaus, et al., 1992DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
15.5 ± 0.05293.GSVerevkin, Beckhaus, et al., 1992Steele and coworkers in reference Steele, Chirico, et al., 2002 refer to a personal communication with one of the authors of Verevkin, Beckhaus, et al., 1992—stating that it was established that the compound studied was not diethyl malonate.; AC
15.1305.AStephenson and Malanowski, 1987Based on data from 293. to 318. K.; AC
14.3399.AStephenson and Malanowski, 1987Based on data from 384. to 468. K.; AC
12.2328.AStephenson and Malanowski, 1987Based on data from 313. to 472. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
313. to 472.15.899932864.82213.407Stull, 1947Coefficents calculated by NIST from author's data.

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

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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: John E. Bartmess

De-protonation reactions

C7H11O4- + Hydrogen cation = Diethyl malonate

By formula: C7H11O4- + H+ = C7H12O4

Quantity Value Units Method Reference Comment
Δr348.3 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase
Δr344.7 ± 1.2kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Δr342.3 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

References

Go To: Top, Gas phase thermochemistry data, 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.

Stewart, 2004
Stewart, J.J.P., Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation, J. Mol. Model, 2004, 10, 1, 6-10, https://doi.org/10.1007/s00894-003-0157-6 . [all data]

Verevkin, Beckhaus, et al., 1992
Verevkin, S.P.; Beckhaus, H.-D.; Ruchardt, C., Geminale substituenteneffekte Teil 5α. Standardbildungsenthalpien von alkylsubstituierten Malonsaure- und α-aminocarbonsaureestern, Thermochim. Acta, 1992, 197, 27-39. [all data]

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]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Palomaa and Mikkila, 1942
Palomaa, M.H.; Mikkila, I., Etherlike Compounds XXVII Turbid Phases in Compounds with Reactivity Minimums, Chem. Ber., 1942, 75B, 1659-67. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 1,4-Diisopropylbenzene, 1,2,4,5-Tetraisopropylbenzene, Cyclohexanone Oxime, Dimethyl Malonate, Glutaric Acid, and Pimelic Acid, J. Chem. Eng. Data, 2002, 47, 4, 725-739, https://doi.org/10.1021/je010088b . [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 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

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