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Cyclooctanone

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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), UV/Visible 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-272.2 ± 1.8kJ/molCcbWolf, 1972Hfusion=0.655±0.025 kcal/mol; ALS
Deltafgas-272. ± 5.4kJ/molCcbRuzieka and Schlapfer, 1933Heat of formation derived by Cox and Pilcher, 1970; ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
42.250.Thermodynamics Research Center, 1997p=1 bar.; GT
61.6100.
82.4150.
104.5200.
141.1273.15
154.4298.15
155.4300.
209.1400.
257.4500.
298.2600.
332.3700.
360.9800.
385.2900.
405.71000.
423.31100.
438.31200.
451.11300.
462.21400.
471.81500.

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-326. ± 5.0kJ/molCcbRuzieka and Schlapfer, 1933Heat of formation derived by Cox and Pilcher, 1970
Quantity Value Units Method Reference Comment
Deltafsolid-322.3 ± 1.6kJ/molCcbWolf, 1972Hfusion=0.655±0.025 kcal/mol
Quantity Value Units Method Reference Comment
Deltacsolid-4825.6 ± 1.6kJ/molCcbWolf, 1972Hfusion=0.655±0.025 kcal/mol; Corresponding «DELTA»fsolid = -323.32 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-4822.9 ± 5.0kJ/molCcbRuzieka and Schlapfer, 1933Reanalyzed by Cox and Pilcher, 1970, Original value = -4820. kJ/mol; Corresponding «DELTA»fsolid = -326.0 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, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil469.2KN/AWeast and Grasselli, 1989BS
Tboil478.7KN/AWolf, 1972, 2Uncertainty assigned by TRC = 0.5 K; TRC
Tboil469.15KN/AWallach, 1907Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Tfus317.4KN/AWolf, 1972, 2Uncertainty assigned by TRC = 0.1 K; TRC
Tfus298.65KN/AWallach, 1907Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Deltavap54.4kJ/molCGCChickos, Hosseini, et al., 1995Based on data from 343. - 383. K.; AC
Deltavap53.6kJ/molCGCChickos, Hosseini, et al., 1995Based on data from 343. - 383. K.; AC
Deltavap54.2kJ/molCGCChickos, Hosseini, et al., 1995Based on data from 343. - 383. K.; AC
Deltavap48.5 ± 0.6kJ/molN/AWolf, 1972AC
Deltavap54. ± 2.kJ/molVRuzieka and Schlapfer, 1933Heat of formation derived by Cox and Pilcher, 1970; ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
47.3338.AStephenson and Malanowski, 1987Based on data from 323. - 403. K.; AC
46.8409.A,EBStephenson and Malanowski, 1987Based on data from 394. - 484. K. See also Meyer and Hotz, 1976.; AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
14.4174.Gonthier-Vassal and Szwarc, 1998CAL
60.8226.8
9.0318.7

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: 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

Hydrogen + Cyclooctanone = Cyclooctyl alcohol

By formula: H2 + C8H14O = C8H16O

Quantity Value Units Method Reference Comment
Deltar-55.73kJ/molChydWiberg, Crocker, et al., 1991liquid phase
Deltar-53.14kJ/molChydWiberg, Crocker, et al., 1991solid phase
Deltar-39.0kJ/molChydWiberg, Crocker, et al., 1991gas phase
Deltar-53.14 ± 0.59kJ/molCmWiberg, Crocker, et al., 1991solid 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C8H14O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)849.4kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity819.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.28PESpanka, Boese, et al., 1987Vertical value; LBLHLM
9.28PESpanka and Rademacher, 1986Vertical value; LBLHLM
9.08PEKovac and Klasinc, 1978Vertical value; LLK
9.00PEHentrich, Gunkel, et al., 1974Vertical value; LLK
9.09 ± 0.02PEChadwick, Frost, et al., 1971Vertical value; LLK

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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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)

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

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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-1282
NIST MS number 230705

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

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, Notes

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, Eugeny B. Stern, Antonina A. Goncharova, 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 O'Sullivan and Testa, 1973
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. 2277
Instrument Bausch and Lomb 505 or Beckman DU
Melting point 29
Boiling point 196

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), UV/Visible spectrum, Notes

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

Wolf, 1972
Wolf, G., Thermochemische Untersuchungen an cyclischen Ketonen, Helv. Chim. Acta, 1972, 55, 1446-1459. [all data]

Ruzieka and Schlapfer, 1933
Ruzieka, L.; Schlapfer, P., Zur kenntnis des kohlenstoffringes XXII. Uber die verbrennungswarme bei hochgliedrigen ringverbindungen, Helv. Chim. Acta, 1933, 16, 162-169. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [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]

Wolf, 1972, 2
Wolf, G., Thermochemical studies of cyclic ketones, Helv. Chim. Acta, 1972, 55, 1446. [all data]

Wallach, 1907
Wallach, O., Justus Liebigs Ann. Chem., 1907, 353, 331. [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]

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]

Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A., Cohesive energies in polar organic liquids. 3. Cyclic ketones, J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035 . [all data]

Gonthier-Vassal and Szwarc, 1998
Gonthier-Vassal, A.; Szwarc, H., Thermochim. Acta, 1998, 141. [all data]

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [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]

Spanka, Boese, et al., 1987
Spanka, G.; Boese, R.; Rademacher, P., Transannualr interactions in difunctional medium rings. 2. Molecular structure and conformational properties of 1-alkylhexahydroazocin-5-ones, J. Org. Chem., 1987, 52, 3362. [all data]

Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P., Transannular interactions in difunctional medium rings. 1. n/«pi» Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy, J. Org. Chem., 1986, 51, 592. [all data]

Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L., Photoelectron spectroscopy of adamantane and some adamantanones, Croat. Chem. Acta, 1978, 51, 55. [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]

Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L., The photoelectron spectra of cyclic ketones, Tetrahedron Lett., 1971, 47, 4543. [all data]

O'Sullivan and Testa, 1973
O'Sullivan, M.; Testa, A.C., Fluorescence of cycloalkanones, J. Phys. Chem., 1973, 77, 15, 1830-1833. [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), UV/Visible spectrum, References