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2-Propynoic acid, methyl ester


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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil377.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil376. - 378.KN/AFarchan Laboratories, 1990BS
Quantity Value Units Method Reference Comment
Deltavap28.9kJ/molCGCChickos, Hosseini, et al., 1995Based on data from 313. - 363. K.; AC
Deltavap35.6 ± 0.4kJ/molGCAzandegbe, 1987AC
Deltavap36.3 ± 0.3kJ/molGCCFuchs and Peacock, 1980AC
Deltavap35.9 ± 0.1kJ/molCSvoboda, Uchytilová, et al., 1980AC
Deltavap35.8 ± 0.1kJ/molCSunner, Svensson, et al., 1979AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
39.1246.AStephenson and Malanowski, 1987Based on data from 231. - 353. K.; AC
32.8368.AStephenson and Malanowski, 1987Based on data from 353. - 486. K.; AC
35.9308.AStephenson and Malanowski, 1987Based on data from 293. - 353. K. See also Polák and Mertl, 1965.; AC
34.9 ± 0.1313.CSvoboda, Uchytilová, et al., 1980AC
34.2 ± 0.1326.CSvoboda, Veselý, et al., 1977AC
33.8 ± 0.1331.CSvoboda, Veselý, et al., 1977AC
32.8 ± 0.1344.CSvoboda, Veselý, et al., 1977AC
32.1 ± 0.1355.CSvoboda, Veselý, et al., 1977AC
31.5 ± 0.1363.CSvoboda, Veselý, et al., 1977AC

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

C4H3O2- + Hydrogen cation = 2-Propynoic acid, methyl ester

By formula: C4H3O2- + H+ = C4H4O2

Quantity Value Units Method Reference Comment
Deltar1501. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1469. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; B

1,3 Diphenylisobenzofuran + 2-Propynoic acid, methyl ester = C24H18O3

By formula: C20H14O + C4H4O2 = C24H18O3

Quantity Value Units Method Reference Comment
Deltar-123.kJ/molKinSamuilov, Nurullina, et al., 1983liquid phase; solvent: Dichloroethane; ALS

2Hydrogen + 2-Propynoic acid, methyl ester = Methyl propionate

By formula: 2H2 + C4H4O2 = C4H8O2

Quantity Value Units Method Reference Comment
Deltar-331. ± 4.6kJ/molChydFlitcroft and Skinner, 1958liquid phase; solvent: Ethanol; ALS

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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-1585
NIST MS number 227663

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References

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

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

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Azandegbe, 1987
Azandegbe, E.C., Analusis, 1987, 15, 370. [all data]

Fuchs and Peacock, 1980
Fuchs, Richard; Peacock, L. Alan, Heats of vaporization of esters by the gas chromatography--calorimetry method, Can. J. Chem., 1980, 58, 24, 2796-2799, https://doi.org/10.1139/v80-447 . [all data]

Svoboda, Uchytilová, et al., 1980
Svoboda, Václav; Uchytilová, Vera; Majer, Vladimír; Pick, Jirí, Heats of vaporization of alkyl esters of formic, acetic and propionic acids, Collect. Czech. Chem. Commun., 1980, 45, 12, 3233-3240, https://doi.org/10.1135/cccc19803233 . [all data]

Sunner, Svensson, et al., 1979
Sunner, S.; Svensson, Ch.; Zelepuga, A.S., Enthalpies of vaporization at 298.15 K for some 2-alkanones and methyl alkanoates, J. Chem. Thermodyn., 1979, 11, 491-495. [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]

Polák and Mertl, 1965
Polák, J.; Mertl, I., Saturated vapour pressure of methyl acetate, ethyl acetate, n-propyl acetate, methyl propionate, and ethyl propionate, Collect. Czech. Chem. Commun., 1965, 30, 10, 3526-3528, https://doi.org/10.1135/cccc19653526 . [all data]

Svoboda, Veselý, et al., 1977
Svoboda, V.; Veselý, F.; Holub, R.; Pick, J., Heats of vaporization of alkyl acetates and propionates, Collect. Czech. Chem. Commun., 1977, 42, 3, 943-951, https://doi.org/10.1135/cccc19770943 . [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [all data]

Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [all data]


Notes

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