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Ethyl cyanoacetate

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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 as indicated in comments:
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
Deltafliquid-330.3kJ/molCcbGuinchant, 1918Author hf288_condensed[kcal/mol]=-82.70 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2638.kJ/molCcbGuinchant, 1918Author hf288_condensed[kcal/mol]=-82.70 kcal/mol; ALS
Quantity Value Units Method Reference Comment
liquid275.33J/mol*KN/AIskhakov, Ismailov, et al., 1991S value does not agree with 87 KHO/BUG.; DH
liquid177.45J/mol*KN/AKhodzhaeva, Bugakov, et al., 1987S value does not agree with 91ISK/ISM.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
222.04300.Iskhakov, Ismailov, et al., 1991T = 90 to 300 K.; DH
220.22298.15Khodzhaeva, Bugakov, et al., 1987T = 90 to 300 K.; DH

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, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil482.2KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus371.65KN/APopp, 1964Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple247.0KN/AIskhakov, Ismailov, et al., 1991, 2Uncertainty assigned by TRC = 1. K; TRC
Ttriple160.KN/AIskhakov, Ismailov, et al., 1991, 2Glass phase; Uncertainty assigned by TRC = 1. K; TRC
Ttriple246.8KN/AKhodzhaeva, Bugakov, et al., 1987, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
66.9355.AStephenson and Malanowski, 1987Based on data from 340. - 479. K. See also Stull, 1947.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
341.0 - 479.7.467243693.66316.138Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
11.78246.8Domalski and Hearing, 1996AC

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
162.5crystaline, IIcrystaline, IKhodzhaeva, Bugakov, et al., 1987Glass transition. Transition temperature estimated from graph.; DH

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
11.780246.8crystaline, IliquidKhodzhaeva, Bugakov, et al., 1987DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
47.73246.8crystaline, IliquidKhodzhaeva, Bugakov, et al., 1987DH

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:


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 by: John E. Bartmess

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

C5H6NO2- + Hydrogen cation = Ethyl cyanoacetate

By formula: C5H6NO2- + H+ = C5H7NO2

Quantity Value Units Method Reference Comment
Deltar1422. ± 9.6kJ/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar1396. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase

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

C5H6NO2- + Hydrogen cation = Ethyl cyanoacetate

By formula: C5H6NO2- + H+ = C5H7NO2

Quantity Value Units Method Reference Comment
Deltar1422. ± 9.6kJ/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar1396. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass 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-1495
NIST MS number 228301

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillarySE-54959.Weber, 198625. m/0.31 mm/0.17 «mu»m, H2, 2. K/min; Tstart: 35. C
CapillarySE-54960.Weber, 198625. m/0.31 mm/0.17 «mu»m, H2, 2. K/min; Tstart: 35. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5962.Jung, Wichmann, et al., 199925. m/0.20 mm/0.33 «mu»m, 50. C @ 3. min, 5. K/min; Tend: 180. C

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [all data]

Iskhakov, Ismailov, et al., 1991
Iskhakov, B.G.; Ismailov, T.S.; Khodzhaeva, M.G.; Igamberdyev, Kh.T.; Mamadalimov, A.T., Heat capacity of cyanoacetic acid ethyl ester, Inzh.-Fiz. Zh., 1991, 61(3), 427-430. [all data]

Khodzhaeva, Bugakov, et al., 1987
Khodzhaeva, M.G.; Bugakov, Yu.V.; Ismailov, T.S., Heat capacity and thermodynamic functions of ethyl cyanoacetate, Khim.-Farm. Zhur., 1987, 21, 760-762. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Popp, 1964
Popp, F.D., Some Derivatives of 3-Bromobenzaldehyde, J. Chem. Eng. Data, 1964, 9, 381. [all data]

Iskhakov, Ismailov, et al., 1991, 2
Iskhakov, B.G.; Ismailov, T.S.; Khodzhaeva, M.G.; Igamberdyev, K.T.; Mamadalimov, A.T., Heat capacity of cyanoacetic acid ethyl ester, Inzh.-Fiz. Zh., 1991, 61, 427-30. [all data]

Khodzhaeva, Bugakov, et al., 1987, 2
Khodzhaeva, M.G.; Bugakov, Yu.V.; Ismailov, T.S., Heat capacity and thermodynamic functions of ethyl cyanoacetate, Khim.-Farm. Zh., 1987, 21, 760-2. [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]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Weber, 1986
Weber, L., Utilization of the Sadtler standard RI system in micropollution analyses, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 446-451, https://doi.org/10.1002/jhrc.1240090806 . [all data]

Jung, Wichmann, et al., 1999
Jung, A.; Wichmann, K.-H.; Kolb, M., VOC emission of polymeric packaging materials, LaborPraxis, 1999, 23, 9, 20-22. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References