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Cycloheptanone

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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 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-248. ± 1.3kJ/molCcbWolf, 1972ALS
Deltafgas-247. ± 2.kJ/molCcbSkuratov and Shtekher, 1958Heat of formation derived by Cox and Pilcher, 1970; ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
46.8550.Thermodynamics Research Center, 1997p=1 bar.; GT
57.50100.
74.03150.
93.15200.
125.80273.15
137.78298.15
138.68300.
186.14400.
228.00500.
262.84600.
291.71700.
315.87800.
336.27900.
353.601000.
368.41100.
381.11200.
392.01300.
401.31400.
409.41500.

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-297.6 ± 1.1kJ/molCcbWolf, 1972 
Deltafliquid-299. ± 1.kJ/molCcbSkuratov and Shtekher, 1958Heat of formation derived by Cox and Pilcher, 1970
Quantity Value Units Method Reference Comment
Deltacliquid-4172.0 ± 1.0kJ/molCcbWolf, 1972Corresponding «DELTA»fliquid = -297.57 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-4172.kJ/molCcbSkuratov, Kozina, et al., 1958Corresponding «DELTA»fliquid = -297. kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-4170.2 ± 1.3kJ/molCcbSkuratov and Shtekher, 1958Reanalyzed by Cox and Pilcher, 1970, Original value = -4153. ± 0.1 kJ/mol; Corresponding «DELTA»fliquid = -299.4 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-4203.2kJ/molCcbZubova, 1901Corresponding «DELTA»fliquid = -266. 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
Tboil451.7KN/AWeast and Grasselli, 1989BS
Tboil452.95KN/AWolf, 1972, 2Uncertainty assigned by TRC = 0.6 K; TRC
Tboil453.15KN/AWallach, 1907Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Deltavap51. ± 2.kJ/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
48.5328.AStephenson and Malanowski, 1987Based on data from 313. - 453. K.; AC
44.8388.A,EBStephenson and Malanowski, 1987Based on data from 373. - 465. K. See also Meyer and Hotz, 1976.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
1.39259.3Gonthier-Vassal and Szwarc, 1998AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
54.6227.Gonthier-Vassal and Szwarc, 1998, 2CAL
1.8232.6
5.4259.3

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
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

C7H11O- + Hydrogen cation = Cycloheptanone

By formula: C7H11O- + H+ = C7H12O

Quantity Value Units Method Reference Comment
Deltar1537. ± 9.2kJ/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar1506. ± 10.kJ/molH-TSZimmerman, Jackson, et al., 1978gas phase; B

Hydrogen + Cycloheptanone = Cycloheptanol

By formula: H2 + C7H12O = C7H14O

Quantity Value Units Method Reference Comment
Deltar-62.5 ± 0.4kJ/molChydWiberg, Crocker, et al., 1991liquid phase; ALS
Deltar-46. ± 1.kJ/molChydWiberg, Crocker, et al., 1991gas phase; ALS

3Hydrogen + 2,4,6-Cycloheptatrien-1-one = Cycloheptanone

By formula: 3H2 + C7H6O = C7H12O

Quantity Value Units Method Reference Comment
Deltar-282.8 ± 1.3kJ/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid; 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
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C7H12O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)845.6kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity815.9kJ/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
846.3 ± 0.2Tabrizchi and Shooshtari, 2003T = 403-446K; Authors report only relative PAs. Absolute values are referenced here to PA(CH3COOC2H5) = 835.7 kJ/mol as listed in Hunter and Lias, 1998, although average PA(CH3COOC2H5) from the literature sources in Hunter and Lias, 1998 is 831.0 kJ/mol; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.49 ± 0.01PECocksey, Eland, et al., 1971LLK
9.14PEHentrich, Gunkel, et al., 1974Vertical value; LLK
9.17 ± 0.02PEChadwick, Frost, et al., 1971Vertical value; LLK

De-protonation reactions

C7H11O- + Hydrogen cation = Cycloheptanone

By formula: C7H11O- + H+ = C7H12O

Quantity Value Units Method Reference Comment
Deltar1537. ± 9.2kJ/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar1506. ± 10.kJ/molH-TSZimmerman, Jackson, et al., 1978gas phase; 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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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)

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

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

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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- 952
NIST MS number 230264

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

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L130.1009.Wehrli and Kováts, 1959Celite; Column length: 2.25 m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryRTX-51005.1Ádámová, Orinák, et al., 200530. m/0.25 mm/0.25 «mu»m, N2, 40. C @ 2. min, 5. K/min, 300. C @ 10. min
CapillaryRTX-51015.5Ádámová, Orinák, et al., 200530. m/0.25 mm/0.25 «mu»m, N2, 40. C @ 2. min, 5. K/min, 300. C @ 10. min

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPolydimethyl siloxane105.992.Tello, Lebron-Aguilar, et al., 2009 
CapillaryPolydimethyl siloxane75.979.Tello, Lebron-Aguilar, et al., 2009 
CapillaryPolydimethyl siloxane90.985.Tello, Lebron-Aguilar, et al., 2009 
CapillaryMethyl Silicone100.989.Lebrón-Aguilar, Quintanilla-López, et al., 2007 
CapillaryMethyl Silicone120.999.Lebrón-Aguilar, Quintanilla-López, et al., 2007 
CapillaryMethyl Silicone140.1008.Lebrón-Aguilar, Quintanilla-López, et al., 2007 
CapillaryMethyl Silicone80.981.Lebrón-Aguilar, Quintanilla-López, et al., 2007 

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

View large format table.

Column type Active phase I Reference Comment
CapillaryRTX-51015.Ádámová, Orinák, et al., 200530. m/0.25 mm/0.25 «mu»m, N2; Program: not specified
CapillaryRTX-51015.Ádámová, Orinák, et al., 200530. m/0.25 mm/0.25 «mu»m, N2; Program: not specified
CapillaryMethyl Silicone987.Zenkevich, 1998Program: not specified
CapillaryOV-11010.Ramsey and Flanagan, 1982Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1495.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, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]

Skuratov and Shtekher, 1958
Skuratov, S.M.; Shtekher, S.M., On the heat combustion of cycloheptanone, Trans. Faraday Soc., 1958, 4883. [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]

Skuratov, Kozina, et al., 1958
Skuratov, S.M.; Kozina, M.P.; Shtocher, S.M.; Prevalova, N.M.; Kamkina, L.S.; Zuko, V.D., Heats of combustion of cyclic compounds, Bull. Chem. Thermodyn., 1958, 1, 21. [all data]

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

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, Anne; Szwarc, Henri, Thermodynamic properties of cycloketones: A DSC study, Thermochimica Acta, 1998, 320, 1-2, 141-154, https://doi.org/10.1016/S0040-6031(98)00409-2 . [all data]

Gonthier-Vassal and Szwarc, 1998, 2
Gonthier-Vassal, A.; Szwarc, H., Thermochim. Acta, 1998, 141. [all data]

Zimmerman, Jackson, et al., 1978
Zimmerman, A.H.; Jackson, R.L.; Janousek, B.K.; Brauman, J.J., Electron photodetachment from cyclic enolate anions in the gas phase: Electron affinities of cyclic enolate radicals, J. Am. Chem. Soc., 1978, 100, 4674. [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]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Doering, W.E.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of hydrogenation. III. Hydrogenation of cycllooctatetraene and of some seven-membered non-benzenoid aromatic compounds, J. Am. Chem. Soc., 1957, 79, 4127-4133. [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]

Tabrizchi and Shooshtari, 2003
Tabrizchi, M.; Shooshtari, S., Proton affinity measurements using ion mobility spectrometry, J. Chem. Thermodynamics, 2003, 35, 863. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [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]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L., Retention indices as identification tool in pyrolysis-capillary gas chromatography, J. Chromatogr. A, 2005, 1087, 1-2, 131-141, https://doi.org/10.1016/j.chroma.2005.01.003 . [all data]

Tello, Lebron-Aguilar, et al., 2009
Tello, A.M.; Lebron-Aguilar, R.; Quintanilla-Lopez, J.E.; Santiuste, J.M., Isothermal retention indices on poly93-cyanopropylmethyl)siloxane stationary phases, J. Chromatogr. A, 2009, 1216, 10, 1630-1639, https://doi.org/10.1016/j.chroma.2008.10.025 . [all data]

Lebrón-Aguilar, Quintanilla-López, et al., 2007
Lebrón-Aguilar, R.; Quintanilla-López, J.E.; Tello, A.M.; Santiuste, J.M., Isothermal retention indices on poly (3,3,3-trifluoropropylmethylsiloxane) stationary phases, J. Chromatogr. A, 2007, 1160, 1-2, 276-288, https://doi.org/10.1016/j.chroma.2007.05.025 . [all data]

Zenkevich, 1998
Zenkevich, I.G., Non-Traditional Criteria for Gas-Chromatographic and Chromato-Mass-Spectrometric Identification of Organic Compounds, Zh. Anal. Khim., 1998, 53, 8, 828-835. [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, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References