Cyclohexanone

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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, 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-231.1 ± 0.88kJ/molCmWiberg, Crocker, et al., 1991ALS
Δfgas-225.7kJ/molEqkKabo, Yursha, et al., 1988ALS
Δfgas-227.7 ± 1.9kJ/molCcbWolf, 1972ALS
Δfgas-226.3kJ/molCcbSellers and Sunner, 1962ALS
Quantity Value Units Method Reference Comment
gas335.53J/mol*KN/AKabo G.J., 1988GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
121.06298.15Kabo G.J., 1988Selected thermodynamic functions are in better agreement with experimental values of S(298.15 K) and Cp(T) than statistical values calculated by [ Thermodynamics Research Center, 1997, Andreevskii D.N., 1976]. Maximum discrepancies with functions given in [ Thermodynamics Research Center, 1997] amount to 2.5 and 5.0 J/mol*K for S(T) and Cp(T), respectively. Discrepancies with data [ Andreevskii D.N., 1976] reach 11 and 8 J/mol*K for S(T) and Cp(T), respectively.; GT
121.89300.
161.88400.
196.39500.
225.24600.
249.27700.
269.47800.
286.51900.
301.061000.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
155.20385.Shvaro O.V., 1987The experimental values of Cp(T) obtained by [ Vilcu R., 1975] seem to be not enough reliable in view of the comparison of experimental heat capacities of some alcohols and ketones measured by these authors (see [ Kabo G.J., 1995]).; GT
161.07400.
168.98420.
175.81440.
183.65460.
190.18480.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid-276.1 ± 0.84kJ/molCmWiberg, Crocker, et al., 1991ALS
Δfliquid-272.6 ± 1.8kJ/molCcbWolf, 1972ALS
Δfliquid-254. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962ALS
Δfliquid-271.4kJ/molCcbSellers and Sunner, 1962ALS
Quantity Value Units Method Reference Comment
Δcliquid-3517.6 ± 1.7kJ/molCcbWolf, 1972Corresponding Δfliquid = -272.58 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3536. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962Corresponding Δfliquid = -254. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3518.9 ± 1.0kJ/molCcbSellers and Sunner, 1962Corresponding Δfliquid = -271.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3499. ± 0.8kJ/molCcbSkuratov, Kozina, et al., 1957At 20C; Corresponding Δfliquid = -291. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid229.03J/mol*KN/ANakamura, Suga, et al., 1980DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
177.20300.Nakamura, Suga, et al., 1980T = 13 to 300 K. Unsmoothed experimental datum for Cp at 296.40 K is 175.96 J/mol*K.; DH
200.4304.2Phillip, 1939DH
177.8290.Herz and Bloch, 1924DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
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
Tboil428. ± 2.KAVGN/AAverage of 21 out of 23 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus243. ± 10.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple245.21KN/ANakamura, Suga, et al., 1980, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple242.4KN/AWuerflinger and Kreutzenbeck, 1978Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tc664.3KN/AQuadri and Kudchadker, 1991Uncertainty assigned by TRC = 3. K; TRC
Tc653.KN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 3. K; TRC
Tc629.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Pc46.00barN/AQuadri and Kudchadker, 1991Uncertainty assigned by TRC = 1.00 bar; TRC
Pc40.00barN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 0.50 bar; TRC
Pc38.5035barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2.0265 bar; TRC
Quantity Value Units Method Reference Comment
Δvap44. ± 4.kJ/molAVGN/AAverage of 7 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
320.20.020Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
45.130428.8N/ASvoboda, Kubes, et al., 1992Value corrected to 298.15 K.; DH
43.1358.EBTeodorescu, Barhala, et al., 2006Based on data from 343. to 427. K.; AC
44.0333.N/AAucejo, Monton, et al., 1993Based on data from 318. to 428. K.; AC
44.4 ± 0.1308.CSvoboda, Kubes, et al., 1992AC
44.0 ± 0.1313.CSvoboda, Kubes, et al., 1992AC
43.4 ± 0.1323.CSvoboda, Kubes, et al., 1992AC
43.1 ± 0.1328.CSvoboda, Kubes, et al., 1992AC
42.2 ± 0.1338.CSvoboda, Kubes, et al., 1992AC
41.8 ± 0.1343.CSvoboda, Kubes, et al., 1992AC
41.4 ± 0.1348.CSvoboda, Kubes, et al., 1992AC
42.2360.EBAmbrose and Ghiassee, 1987, 2Based on data from 345. to 458. K.; AC
41.5377.A,EBStephenson and Malanowski, 1987Based on data from 362. to 439. K. See also Meyer and Hotz, 1973.; AC
40.4410.N/ACastellari, Francesconi, et al., 1984Based on data from 395. to 426. K.; AC
40.3286.N/ARadulescu and Alexa, 1938Based on data from 273. to 298. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
362.78 to 438.924.1033 ± 0.000991495.51 ± 0.67-63.598 ± 0.075Meyer and Hotz, 1973

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Reference Comment
49.3254.Nitta and Seki, 1948Based on data from 243. to 265. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
1.33245.2Nakamura, Suga, et al., 1980AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
38.5221.Gonthier-Vassal and Szwarc, 1998CAL
5.2242.6

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
39.22220.8Nakamura, Suga, et al., 1980, 2CAL
5.42245.2

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
8.6596220.83crystaline, IIcrystaline, INakamura, Suga, et al., 1980DH
1.3276245.21crystaline, IliquidNakamura, Suga, et al., 1980DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
39.22220.83crystaline, IIcrystaline, INakamura, Suga, et al., 1980DH
5.414245.21crystaline, IliquidNakamura, Suga, et al., 1980DH

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, 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

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Δr1533. ± 8.4kJ/molD-EABrinkman, Berger, et al., 1993gas phase; B
Δr1531. ± 9.6kJ/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Δr1544. ± 18.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B
Quantity Value Units Method Reference Comment
Δr1501. ± 9.6kJ/molH-TSBrinkman, Berger, et al., 1993gas phase; B
Δr1498. ± 11.kJ/molH-TSZimmerman, Jackson, et al., 1978gas phase; B
Δr1511. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B

Cyclohexanone + Hydrogen = Cyclohexanol

By formula: C6H10O + H2 = C6H12O

Quantity Value Units Method Reference Comment
Δr-75.86 ± 0.50kJ/molCmWiberg, Crocker, et al., 1991liquid phase; ALS
Δr-63.51 ± 0.63kJ/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -64.5 ± 0.3 kJ/mol; At 355 K; ALS

Cyclohexanol = Cyclohexanone + Hydrogen

By formula: C6H12O = C6H10O + H2

Quantity Value Units Method Reference Comment
Δr63.4 ± 2.3kJ/molEqkKabo, Yursha, et al., 1988gas phase; Dehydrogenation; ALS

Water + Cyclohexene, 1-methoxy- = Cyclohexanone + Methyl Alcohol

By formula: H2O + C7H12O = C6H10O + CH4O

Quantity Value Units Method Reference Comment
Δr-13.63 ± 0.69kJ/molEqkHine and Arata, 1976liquid phase; ALS

Water + Cyclohexane, 1,1-dimethoxy- = Cyclohexanone + 2Methyl Alcohol

By formula: H2O + C8H16O2 = C6H10O + 2CH4O

Quantity Value Units Method Reference Comment
Δr28.9 ± 0.1kJ/molCmWiberg, Morgan, et al., 1994liquid phase; ALS

Cyclohexanol + Acetone = Cyclohexanone + Isopropyl Alcohol

By formula: C6H12O + C3H6O = C6H10O + C3H8O

Quantity Value Units Method Reference Comment
Δr9.9 ± 1.9kJ/molEqkFedoseenko, Yursha, et al., 1983gas phase; At 503 K; ALS

Cyclohexanone + 2Methyl Alcohol = Water + Cyclohexane, 1,1-dimethoxy-

By formula: C6H10O + 2CH4O = H2O + C8H16O2

Quantity Value Units Method Reference Comment
Δr-54. ± 1.kJ/molCmWiberg, Morgan, et al., 1994gas phase; ALS

Cyclohexanone + Cyclopentanol = Cyclohexanol + Cyclopentanone

By formula: C6H10O + C5H10O = C6H12O + C5H8O

Quantity Value Units Method Reference Comment
Δr-11.6 ± 1.7kJ/molEqkFedoseenko, Yursha, et al., 1984gas phase; ALS

Cyclohexanone + Isopropyl Alcohol = Cyclohexanol + Acetone

By formula: C6H10O + C3H8O = C6H12O + C3H6O

Quantity Value Units Method Reference Comment
Δr-9.9 ± 1.9kJ/molEqkKabo, Yursha, et al., 1988gas phase; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H10O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.16 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)841.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity811.2kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.0033EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 3.3 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.18PELoudet, Grimaud, et al., 1976LLK
9.5 ± 0.2EIFortin, Forest, et al., 1973LLK
9.16 ± 0.01PECocksey, Eland, et al., 1971LLK
9.14 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.14 ± 0.03PIVilesov, 1960RDSH
9.29PESpanka and Rademacher, 1986Vertical value; LBLHLM
9.18PEKovac and Klasinc, 1978Vertical value; LLK
9.28PEHentrich, Gunkel, et al., 1974Vertical value; LLK
9.14 ± 0.02PEChadwick, Frost, et al., 1971Vertical value; LLK

De-protonation reactions

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Δr1533. ± 8.4kJ/molD-EABrinkman, Berger, et al., 1993gas phase; B
Δr1531. ± 9.6kJ/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Δr1544. ± 18.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B
Quantity Value Units Method Reference Comment
Δr1501. ± 9.6kJ/molH-TSBrinkman, Berger, et al., 1993gas phase; B
Δr1498. ± 11.kJ/molH-TSZimmerman, Jackson, et al., 1978gas phase; B
Δr1511. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

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]

Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [all data]

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

Sellers and Sunner, 1962
Sellers, P.; Sunner, S., Heats of combustion of cyclic ketones and alcohols, Acta Chem. Scand., 1962, 16, 46-52. [all data]

Kabo G.J., 1988
Kabo G.J., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [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]

Andreevskii D.N., 1976
Andreevskii D.N., Thermodynamic properties of C4-C6 cyclic ketones, Zh. Prikl. Khim., 1976, 49, 1819-1823. [all data]

Shvaro O.V., 1987
Shvaro O.V., Thermodynamic properties of cyclopentanone and cyclohexanone, Inzh.-Fiz. Zh., 1987, 52, 807-812. [all data]

Vilcu R., 1975
Vilcu R., Heat capacity of cyclohexanone and 4-methylcyclohexanone in the vapor phase, Rev. Chim. (Bucharest), 1975, 26, 129-131. [all data]

Kabo G.J., 1995
Kabo G.J., Thermodynamic properties, conformation, and phase transitions of cyclopentanol, J. Chem. Thermodyn., 1995, 27, 953-967. [all data]

Rabinovoch, Tel'noy, et al., 1962
Rabinovoch, N.B.; Tel'noy, V.I.; Terman, L.M.; Kirillova, A.S.; Razuvaev, G.A., The heats of decomposition and formation of dicyclohexyl- and dimethylperoxidecarbonate, Dokl. Akad. Nauk SSSR, 1962, 143, 133-136. [all data]

Skuratov, Kozina, et al., 1957
Skuratov, S.M.; Kozina, M.L.; Shteher, S.M.; Varushyenko, R.M., The heats of combustion of several purified compounds, Thermochem. Bull. (Moscow State Univ.), March, 1957, 36-37. [all data]

Nakamura, Suga, et al., 1980
Nakamura, N.; Suga, H.; Seki, S., Calorimetric study on orientationally disordered crystals. Cyclohexene oxide and cyclohexanone, Bull. Chem. Soc. Japan, 1980, 53(10), 2755-2761. [all data]

Phillip, 1939
Phillip, N.M., Adiabatic and isothermal compressibilities of liquids, Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]

Herz and Bloch, 1924
Herz, W.; Bloch, W., Physikalisch-chemische Untersuchungen an Verbindungen der Cyklohexanreihe, Z. Phys. Chem., 1924, 110, 23-39. [all data]

Nakamura, Suga, et al., 1980, 2
Nakamura, N.; Suga, H.; Seki, S., Calorimetric study on orientationally disordered crystals. Cyclohexene oxide and cyclohexanone., Bull. Chem. Soc. Japan, 1980, 53, 10, 2755, https://doi.org/10.1246/bcsj.53.2755 . [all data]

Wuerflinger and Kreutzenbeck, 1978
Wuerflinger, A.; Kreutzenbeck, J., J. Phys. Chem. Solids, 1978, 39, 193. [all data]

Quadri and Kudchadker, 1991
Quadri, S.K.; Kudchadker, A.P., Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable esters, ketones, and ethers, J. Chem. Thermodyn., 1991, 23, 129-34. [all data]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressures and Critical Temperatures and Critical Pressures of C5 and C6 Cyclic Alcohols and Ketones, J. Chem. Thermodyn., 1987, 19, 903. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [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]

Svoboda, Kubes, et al., 1992
Svoboda, V.; Kubes, V.; Basarova, P., Enthalpies of vaporization and cohesive energies of hexan-2-one, 2-methylpentan-4-one, 2,2-dimethylbutan-3-one, 2,6-dimethylheptan-4-one and cyclohexanone, J. Chem. Thermodynam., 1992, 24, 333-336. [all data]

Teodorescu, Barhala, et al., 2006
Teodorescu, Mariana; Barhala, Alexandru; Dragoescu, Dana, Isothermal (vapour+liquid) equilibria for the binary (cyclopentanone or cyclohexanone with 1,1,2,2-tetrachloroethane) systems at temperatures of (343.15, 353.15, and 363.15)K, The Journal of Chemical Thermodynamics, 2006, 38, 11, 1432-1437, https://doi.org/10.1016/j.jct.2006.01.010 . [all data]

Aucejo, Monton, et al., 1993
Aucejo, Antonio; Monton, Juan B.; Munoz, Rosa; Sanchotello, Margarita, Isobaric vapor-liquid equilibrium data for the cyclohexanone + N-methylacetamide system, J. Chem. Eng. Data, 1993, 38, 1, 160-162, https://doi.org/10.1021/je00009a039 . [all data]

Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B., Vapour pressures and critical temperatures and critical pressures of C5 and C6 cyclic alcohols and ketones, The Journal of Chemical Thermodynamics, 1987, 19, 9, 903-909, https://doi.org/10.1016/0021-9614(87)90036-X . [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, 1973
Meyer, Edwin F.; Hotz, Roger D., High-precision vapor-pressure data for eight organic compounds, J. Chem. Eng. Data, 1973, 18, 4, 359-362, https://doi.org/10.1021/je60059a008 . [all data]

Castellari, Francesconi, et al., 1984
Castellari, Carlo; Francesconi, Romolo; Comelli, Fabio, Vapor-liquid equilibriums in binary systems containing 1,3-dioxolane at isobaric conditions. 5. Binary mixtures of 1,3-dioxolane with cyclohexanone and cyclohexanol, J. Chem. Eng. Data, 1984, 29, 1, 90-93, https://doi.org/10.1021/je00035a029 . [all data]

Radulescu and Alexa, 1938
Radulescu, D.; Alexa, M., Bull. Chem. Soc. Romania, 1938, 20A, 89. [all data]

Nitta and Seki, 1948
Nitta, I.; Seki, S., J. Chem. Soc. Jpn. Pure Chem. Sect., 1948, 69, 141. [all data]

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

Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I., Molecular Rotation and the Observation of Dipole-Bound States of Anions, J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688 . [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]

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]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

Hine and Arata, 1976
Hine, J.; Arata, K., Keto-Enol tautomerism. II. The calorimetrical determination of the equilibrium constants for keto-enol tautomerism for cyclohexanone, Bull. Chem. Soc. Jpn., 1976, 49, 3089-3092. [all data]

Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions, Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]

Fedoseenko, Yursha, et al., 1984
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium of cyclopentanol dehydrogenation and hydrogen disproportionation in the cyclopentanol-cyclohexanone system, Dokl. Akad. Nauk BSSR, 1984, 28, 1109-1112. [all data]

Hunter and Lias, 1998
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Notes

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