Cyclopropanecarboxylic acid

Data at NIST subscription sites:

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.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
22.65298.16Tabacik V., 1978 
26.429353.16
29.661403.16
32.591453.16

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
Δcliquid-486.4kcal/molCcbBruylants and Stassens, 1921Corresponding Δfliquid = -94.7 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-479.7kcal/molCcbRoth and Ostling, 1913Corresponding Δfliquid = -101.4 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil456.2KN/AWeast and Grasselli, 1989BS
Tboil455. to 457.KN/AFrinton Laboratories Inc., 1986BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
14.1 ± 0.07340.EBSteele, Chirico, et al., 2002Based on data from 357. to 473. K.; AC
13.3 ± 0.05380.EBSteele, Chirico, et al., 2002Based on data from 357. to 473. K.; AC
12.5 ± 0.05420.EBSteele, Chirico, et al., 2002Based on data from 357. to 473. K.; AC
11.7 ± 0.1460.EBSteele, Chirico, et al., 2002Based on data from 357. to 473. K.; AC

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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: 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

C4H5O2- + Hydrogen cation = Cyclopropanecarboxylic acid

By formula: C4H5O2- + H+ = C4H6O2

Quantity Value Units Method Reference Comment
Δr346.0 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Quantity Value Units Method Reference Comment
Δr339.0 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Quantity Value Units Method Reference Comment
Proton affinity (review)196.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity188.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.64PEHolmes, Terlouw, et al., 1979LLK

De-protonation reactions

C4H5O2- + Hydrogen cation = Cyclopropanecarboxylic acid

By formula: C4H5O2- + H+ = C4H6O2

Quantity Value Units Method Reference Comment
Δr346.0 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr339.0 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B

IR Spectrum

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, Notes

Data compiled by: Coblentz Society, Inc.

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


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, IR Spectrum, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291945

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.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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.

Tabacik V., 1978
Tabacik V., Vibrational spectra in cyclopropane series. III. Fundamental modes of cyclopropanecarboxylic acid monomer and of its -OD species, Spectrochim. Acta, 1978, A34, 315-329. [all data]

Bruylants and Stassens, 1921
Bruylants, P.; Stassens, A., Contribution a letude des composes a noyau trimethylenique, Bull. Cl. Sci. Acad. R. Belg., 1921, 7, 702-719. [all data]

Roth and Ostling, 1913
Roth, W.A.; Ostling, G.J., Thermochemische Untersuchungen in der alicyclischen Reihe, Ber., 1913, 46, 309-327. [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]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Measurements of Vapor Pressure, Heat Capacity, and Density along the Saturation Line for Cyclopropane Carboxylic Acid, N , N -Diethylethanolamine, 2,3-Dihydrofuran, 5-Hexen-2-one, Perfluorobutanoic Acid, and 2-Phenylpropionaldehyde, J. Chem. Eng. Data, 2002, 47, 4, 715-724, https://doi.org/10.1021/je010087j . [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [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]

Holmes, Terlouw, et al., 1979
Holmes, J.L.; Terlouw, J.K.; Vijfhuizen, P.C.; A'Campo, C., Metastable ion studies XII-Molecular and fragment ion structures for isomeric C4H6O2 acids, Org. Mass Spectrom., 1979, 14, 204. [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, IR Spectrum, Mass spectrum (electron ionization), References