Cycloheptanone

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 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
Δfgas-59.3 ± 0.31kcal/molCcbWolf, 1972ALS
Δfgas-59.1 ± 0.4kcal/molCcbSkuratov and Shtekher, 1958Heat of formation derived by Cox and Pilcher, 1970; ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
11.2050.Thermodynamics Research Center, 1997p=1 bar.; GT
13.74100.
17.69150.
22.26200.
30.067273.15
32.930298.15
33.145300.
44.489400.
54.493500.
62.820600.
69.720700.
75.495800.
80.370900.
84.5121000.
88.051100.
91.091200.
93.691300.
95.911400.
97.851500.

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
Δfliquid-71.14 ± 0.27kcal/molCcbWolf, 1972 
Δfliquid-71.5 ± 0.3kcal/molCcbSkuratov and Shtekher, 1958Heat of formation derived by Cox and Pilcher, 1970
Quantity Value Units Method Reference Comment
Δcliquid-997.13 ± 0.25kcal/molCcbWolf, 1972Corresponding Δfliquid = -71.121 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-997.2kcal/molCcbSkuratov, Kozina, et al., 1958Corresponding Δfliquid = -71.0 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-996.70 ± 0.30kcal/molCcbSkuratov and Shtekher, 1958Reanalyzed by Cox and Pilcher, 1970, Original value = -992.7 ± 0.03 kcal/mol; Corresponding Δfliquid = -71.55 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-1004.6kcal/molCcbZubova, 1901Corresponding Δfliquid = -63.6 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
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
Δvap12.1 ± 0.5kcal/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
11.6328.AStephenson and Malanowski, 1987Based on data from 313. to 453. K.; AC
10.7388.A,EBStephenson and Malanowski, 1987Based on data from 373. to 465. K. See also Meyer and Hotz, 1976.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
0.332259.3Gonthier-Vassal and Szwarc, 1998AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
13.0227.Gonthier-Vassal and Szwarc, 1998, 2CAL
0.43232.6
1.3259.3

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

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 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
Δr367.4 ± 2.2kcal/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr360.0 ± 2.4kcal/molH-TSZimmerman, Jackson, et al., 1978gas phase; B

Hydrogen + Cycloheptanone = Cycloheptanol

By formula: H2 + C7H12O = C7H14O

Quantity Value Units Method Reference Comment
Δr-14.94 ± 0.09kcal/molChydWiberg, Crocker, et al., 1991liquid phase; ALS
Δr-10.9 ± 0.3kcal/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
Δr-67.58 ± 0.30kcal/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid; ALS

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
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)202.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity195.0kcal/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
202.3 ± 0.05Tabrizchi 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
Δr367.4 ± 2.2kcal/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr360.0 ± 2.4kcal/molH-TSZimmerman, Jackson, et al., 1978gas 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 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

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

IR 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

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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, 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 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.


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.

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]


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