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Ethanone, 1-cyclopropyl-

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-115.3 ± 1.2kJ/molCcbKozina, Timofeeva, et al., 1984 

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid-154.7 ± 1.2kJ/molCcbKozina, Timofeeva, et al., 1984 
Quantity Value Units Method Reference Comment
Deltacliquid-2956.2 ± 1.0kJ/molCcbKozina, Timofeeva, et al., 1984Corresponding «DELTA»fliquid = -154.7 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-2916.kJ/molCcbZubova, 1901Corresponding «DELTA»fliquid = -195. kJ/mol (simple calculation by NIST; no Washburn corrections)

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil387.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil384.4KN/AMajer and Svoboda, 1985 
Tboil387.KN/ABuckingham and Donaghy, 1982BS
Tboil384.KN/AHammond and Todd, 1954Uncertainty assigned by TRC = 3. K; TRC
Tboil384.35KN/AVan Volkenburgh, Greenlee, et al., 1949Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus204.85KN/AVan Volkenburgh, Greenlee, et al., 1949Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Deltavap39.47kJ/molN/AMajer and Svoboda, 1985 
Deltavap39.41 ± 0.09kJ/molCFuchs and Hallman, 1983ALS
Deltavap39.4 ± 0.1kJ/molCFuchs and Hallman, 1983AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
34.07384.4N/AMajer and Svoboda, 1985 
37.6374.AStephenson and Malanowski, 1987Based on data from 361. - 387. K.; AC

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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

C5H7O- + Hydrogen cation = Ethanone, 1-cyclopropyl-

By formula: C5H7O- + H+ = C5H8O

Quantity Value Units Method Reference Comment
Deltar1530. ± 17.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between MeCHO, Me2C=NOH; B
Quantity Value Units Method Reference Comment
Deltar1502. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between MeCHO, Me2C=NOH; B

C5H9O+ + Ethanone, 1-cyclopropyl- = (C5H9O+ bullet Ethanone, 1-cyclopropyl-)

By formula: C5H9O+ + C5H8O = (C5H9O+ bullet C5H8O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Deltar113.kJ/molPHPMSSzulejko and McMahon, 1991gas phase; M
Quantity Value Units Method Reference Comment
Deltar123.J/mol*KPHPMSSzulejko and McMahon, 1991gas phase; M

Furan, 2,3-dihydro-5-methyl- = Ethanone, 1-cyclopropyl-

By formula: C5H8O = C5H8O

Quantity Value Units Method Reference Comment
Deltar-9.6 ± 3.3kJ/molEqkCocks and Egger, 1973gas phase; ALS

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 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)854.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity823.kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.46PEAl-Khafaji and Shanshal, 1977Vertical value; LLK
9.50PEKelder, Cerfontain, et al., 1974Vertical value; LLK

De-protonation reactions

C5H7O- + Hydrogen cation = Ethanone, 1-cyclopropyl-

By formula: C5H7O- + H+ = C5H8O

Quantity Value Units Method Reference Comment
Deltar1530. ± 17.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between MeCHO, Me2C=NOH; B
Quantity Value Units Method Reference Comment
Deltar1502. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between MeCHO, Me2C=NOH; B

Ion clustering 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C5H9O+ + Ethanone, 1-cyclopropyl- = (C5H9O+ bullet Ethanone, 1-cyclopropyl-)

By formula: C5H9O+ + C5H8O = (C5H9O+ bullet C5H8O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Deltar113.kJ/molPHPMSSzulejko and McMahon, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar123.J/mol*KPHPMSSzulejko and McMahon, 1991gas 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 NIST Mass Spectrometry Data Center, 1990.
NIST MS number 118795

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

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

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySPB-1704.Flanagan, Streete, et al., 199760. m/0.53 mm/5. «mu»m, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillaryPolydimethyl siloxanes706.Zenkevich and Chupalov, 1996Program: not specified
CapillarySPB-1704.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 «mu»m, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
CapillarySPB-1730.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 «mu»m, Helium; Program: not specified
CapillaryOV-1730.Ramsey and Flanagan, 1982Program: not specified

References

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

Kozina, Timofeeva, et al., 1984
Kozina, M.P.; Timofeeva, L.P.; Gal'chenko, G.L.; Balenkova, E.S.; Ordubadi, M.D., Enthalpies of combustion and formation of 1-methylnorcamphor and methylcyclopropyl ketone, Moscow Univ. Chem. Bull. (Engl. Transl.), 1984, 25, 41-45. [all data]

Zubova, 1901
Zubova, P., Data about heat of combustion of compound cycle structure, Zh. Fiz. Khim., 1901, 33, 708-722. [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]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Hammond and Todd, 1954
Hammond, G.S.; Todd, R.W., The Low Reactivity of Cyclopropane Derivatives twoard Free Radicals, J. Am. Chem. Soc., 1954, 76, 4081. [all data]

Van Volkenburgh, Greenlee, et al., 1949
Van Volkenburgh, R.; Greenlee, K.W.; Derfer, J.M.; Boord, C.E., The Synthesis of Some Cyclopropane Hydrocarbons From Methyl Cyclopropyl Ketone, J. Am. Chem. Soc., 1949, 71, 172-5. [all data]

Fuchs and Hallman, 1983
Fuchs, R.; Hallman, J.H., Heats of vaporization of some monosubstituted cyclopropane, cyclobutane, and cyclopentane derivatives. Some observations on the enthalpies of isodesmic ring opening reactions of cyclobutane derivatives, Can. J. Chem., 1983, 61, 503-505. [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]

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]

Szulejko and McMahon, 1991
Szulejko, J.E.; McMahon, T.B., A Pulsed Electron Beam, Variable Temperature, High Pressure Mass Spectrometric Reevaluation of the Proton Affinity Difference Between 2-Methylpropene and Ammonia, Int. J. Mass Spectrom. Ion Proc., 1991, 109, 279, https://doi.org/10.1016/0168-1176(91)85109-Y . [all data]

Cocks and Egger, 1973
Cocks, A.T.; Egger, K.W., Gas-phase thermal unimolecular isomerizations of acetylcyclopropane. Part I. The equilibrium between 2,3-dihydro-5-methylfuran and acetylcyclopropane, J. Chem. Soc. Perkin Trans. 2, 1973, 197-199. [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]

Al-Khafaji and Shanshal, 1977
Al-Khafaji, J.A.; Shanshal, M., The photoelectron spectra of cyclopropyl ketones, Z. Naturforsch. A:, 1977, 32, 109. [all data]

Kelder, Cerfontain, et al., 1974
Kelder, J.; Cerfontain, H.; Higginson, B.R.; Lloyd, D.R., Photoelectron and ultraviolet absorption spectra of cyclopropyl conjugated 1,2-diketones, Tetrahedron Lett., 1974, 739. [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [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, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References