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2-Cyclohexen-1-one

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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

Quantity Value Units Method Reference Comment
Tboil441.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil443.2KN/AWeast and Grasselli, 1989BS
Tboil440. - 441.KN/AFrinton Laboratories Inc., 1986BS
Quantity Value Units Method Reference Comment
Tc685.KN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 6. K; derived from fit of obs. vapor pressure; TRC
Quantity Value Units Method Reference Comment
Pc45.30barN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 2.50 bar; derived from fit of obs. vapor pressure; TRC
Quantity Value Units Method Reference Comment
rhoc3.28mol/lN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.21 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap49.5 ± 0.4kJ/molEBSteele, Chirico, et al., 1997, 2Based on data from 335. - 481. K.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
45.0366.EBPalczewska-Tulinska and Oracz, 2006Based on data from 351. - 445. 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 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

cyclohexenone-4-enolate anion + Hydrogen cation = 2-Cyclohexen-1-one

By formula: C6H7O- + H+ = C6H8O

Quantity Value Units Method Reference Comment
Deltar1496. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1464. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale

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

View reactions leading to C6H8O+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.23 ± 0.05PEHolmes, Terlouw, et al., 1979LLK
9.20PESchweig, Vermeer, et al., 1974Vertical value; LLK
9.37PEHentrich, Gunkel, et al., 1974Vertical value; LLK

De-protonation reactions

cyclohexenone-4-enolate anion + Hydrogen cation = 2-Cyclohexen-1-one

By formula: C6H7O- + H+ = C6H8O

Quantity Value Units Method Reference Comment
Deltar1496. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1464. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B

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 Sadtler Research Labs Under US-EPA Contract
State gas

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 NIST Mass Spectrometry Data Center, 1990.
NIST MS number 113010

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.


UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Kovaleva, et al., 1976
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 23321
Instrument Specord UV-Vis
Boiling point 169-171

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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]

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., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturted Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di-tert-butylbenzene, (±)-2-Ethylhexanoic Acid, 1-(m, J. Chem. Eng. Data, 1997, 42, 1021-36. [all data]

Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di- tert -butylbenzene, (±)-2-Ethylhexanoic Acid, 2-(Methylamino)ethanol, Perfluoro- n -heptane, and Sulfolane, J. Chem. Eng. Data, 1997, 42, 6, 1021-1036, https://doi.org/10.1021/je9701036 . [all data]

Palczewska-Tulinska and Oracz, 2006
Palczewska-Tulinska, Marcela; Oracz, Pawel, Vapor Pressures of Hexanal, 2-Methylcyclohexanone, and 2-Cyclohexen-1-one, J. Chem. Eng. Data, 2006, 51, 2, 639-641, https://doi.org/10.1021/je0504358 . [all data]

Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P., 'Kinetic' vs. thermodynamic acidities of enones in the gas phase, J. Org. Chem., 1986, 51, 2173. [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]

Schweig, Vermeer, et al., 1974
Schweig, A.; Vermeer, H.; Weidner, U., A photoelectron spectroscopic study of keto-enol tautomerism in acetylacetones - a new application of photoelectron spectroscopy, Chem. Phys. Lett., 1974, 26, 229. [all data]

Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M., Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen, J. Mol. Struct., 1974, 21, 231. [all data]

Kovaleva, et al., 1976
Kovaleva, V.N., et al., Zhur. Organ. Khim., 1976, 12, 76. [all data]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References