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Cyclohexanone, oxime

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-74.88kJ/molCcbKozyro, Kabo, et al., 1992see Kozyro, Marachuk, et al., 1989

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 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
Deltafsolid-153.2 ± 2.5kJ/molCcbKozyro, Kabo, et al., 1992see Kozyro, Marachuk, et al., 1989; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3779.9 ± 2.3kJ/molCcbKozyro, Kabo, et al., 1992see Kozyro, Marachuk, et al., 1989; ALS
Deltacsolid-3723. ± 4.2kJ/molCcbRunge and Maass, 1953At 293 °K; ALS
Quantity Value Units Method Reference Comment
solid,1 bar185.08J/mol*KN/AKozyro, Kabo, et al., 1992DH
solid,1 bar185.12J/mol*KN/AKozyro, Sheiman, et al., 1991DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
199.38298.15Kozyro, Kabo, et al., 1992T = 6 to 450 K. Cp(c, 300 to 340 K) = -143.81 + 1.6984(T/K) - 1.8334x10-3(T/K)2; CP(liq, 380 to 430 K) = 214.30 + 0.1900(T/K) J/mol*K.; DH
199.34298.15Kozyro, Sheiman, et al., 1991T = 6 to 430 K. Cp(c,J/mol*K) = -143.81 + 1.6984T - 1.8334x10-3xT2 (300 to 340 K); Cp(liq,J/mol*K) = 214.30 + 0.1900T (380 to 430 K).; DH

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
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil481.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus362.KN/AWhite and Bishop, 1940Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Ttriple362.5KN/AKozyro, Kabo, et al., 1992Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC
Ttriple362.5KN/AKozyro, Sheiman, et al., 1991, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Deltavap63.1 ± 1.0kJ/molN/ASteele, Chirico, et al., 2002Based on data from 370. - 385. K.; AC
Quantity Value Units Method Reference Comment
Deltasub79.0 ± 2.0kJ/molN/ASteele, Chirico, et al., 2002AC
Deltasub78.32 ± 0.30kJ/molVKozyro, Kabo, et al., 1992see Kozyro, Marachuk, et al., 1989; ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
58.660367.8N/AKozyro, Kabo, et al., 1992DH
58.7 ± 0.6368.CKozyro, Kabo, et al., 1992AC
59.5 ± 0.5371. - 446.N/AKozyro, Kabo, et al., 1992AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
76.5 ± 1.0378.N/ASteele, Chirico, et al., 2002AC
74.0 ± 0.3354.CKozyro, Kabo, et al., 1992AC
79.9 ± 0.7317.MEKozyro, Kabo, et al., 1992Based on data from 288. - 348. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
12.45362.2Zaitsau, Paulechka, et al., 2008AC
12.7362.5Steele, Chirico, et al., 2002AC
12.7362.6Kozyro, Kabo, et al., 1992AC

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.0140240.8crystaline, IIIcrystaline, IIKozyro, Kabo, et al., 1992DH
0.0937273.4crystaline, IIcrystaline, IKozyro, Kabo, et al., 1992DH
12.700362.5crystaline, IliquidKozyro, Kabo, et al., 1992DH
74.010353.7crystaline, I Kozyro, Kabo, et al., 1992DH
0.0140240.8crystaline, IIIcrystaline, IIKozyro, Sheiman, et al., 1991DH
0.0937273.4crystaline, IIcrystaline, IKozyro, Sheiman, et al., 1991DH
12.700362.5crystaline, IliquidKozyro, Sheiman, et al., 1991DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.06240.8crystaline, IIIcrystaline, IIKozyro, Kabo, et al., 1992DH
0.34273.4crystaline, IIcrystaline, IKozyro, Kabo, et al., 1992DH
0.06240.8crystaline, IIIcrystaline, IIKozyro, Sheiman, et al., 1991DH
0.34273.4crystaline, IIcrystaline, IKozyro, Sheiman, et al., 1991DH

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), 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: 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

Cyclohexanone, oxime = Caprolactam

By formula: C6H11NO = C6H11NO

Quantity Value Units Method Reference Comment
Deltar-105.1 ± 4.2kJ/molCisoKozyro, Marachuk, et al., 1989solid 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 compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C6H11NO+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference
8.97 ± 0.03PIGolubitskii, Kulikov, et al., 1979

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), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


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 NIST Mass Spectrometry Data Center, 1992
NIST MS number 125466

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 Huisgen, Rapp, et al., 1954
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. 3017
Instrument n.i.g.
Melting point 90
Boiling point 206

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.

Kozyro, Kabo, et al., 1992
Kozyro, A.A.; Kabo, G.J.; Krouk, V.S.; Sheiman, M.S.; Yursha, I.A.; Simirsky, V.V.; Krasulin, A.P.; Sevruk, V.M.; Gogolinsky, V.I., Thermodynamic properties of cyclohexanone oxime, J. Chem. Thermodyn., 1992, 24, 883-895. [all data]

Kozyro, Marachuk, et al., 1989
Kozyro, A.A.; Marachuk, L.I.; Krasulin, A.P.; Yursha, I.A.; Kabo, G.Ya., Thermodynamic properties of cyclohexanone oxime and «epsilon»-caprolactam, J. Appl. Chem. USSR, 1989, 62, 547-550. [all data]

Runge and Maass, 1953
Runge, F.; Maass, P., Untersuchungen uber die Beckmann=Umlagerung des Zyklohexanonoxims, Chem. Tech. (Berlin), 1953, 5, 421-424. [all data]

Kozyro, Sheiman, et al., 1991
Kozyro, A.A.; Sheiman, M.S.; Kabo, G.Ya.; Yursha, I.A.; Kruk, V.S., Heat capacity and thermodynamic properties of cyclohexanone oxime, Zh. Prikl. Khim. (Leningrad), 1991, 64(8), 1704-1709. [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]

White and Bishop, 1940
White, A.H.; Bishop, W.S., Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds, J. Am. Chem. Soc., 1940, 62, 8-16. [all data]

Kozyro, Sheiman, et al., 1991, 2
Kozyro, A.A.; Sheiman, M.S.; Kabo, G.Ya.; Yursha, I.A.; Krouk, V.S., Heat capacity and thermodynamic properties of cyclohexanone oxime, Zh. Prikl. Khim. (S.-Peterburg), 1991, 64, 1704-9. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 1,4-Diisopropylbenzene, 1,2,4,5-Tetraisopropylbenzene, Cyclohexanone Oxime, Dimethyl Malonate, Glutaric Acid, and Pimelic Acid, J. Chem. Eng. Data, 2002, 47, 4, 725-739, https://doi.org/10.1021/je010088b . [all data]

Zaitsau, Paulechka, et al., 2008
Zaitsau, Dzmitry H.; Paulechka, Yauheni U.; Kabo, Gennady J.; Blokhin, Andrey V.; Emel'yanenko, Vladimir N.; Verevkin, Sergey P.; Heintz, Andreas, Thermodynamics of Cyclohexanone Oxime, J. Chem. Eng. Data, 2008, 53, 3, 694-703, https://doi.org/10.1021/je700546r . [all data]

Golubitskii, Kulikov, et al., 1979
Golubitskii, A.E.; Kulikov, N.S.; Zyakun, A.M.; Valovoi, V.A.; Alekseev, A.M.; Volkov, V.N., Photoionization mass spectra of alicyclic compounds with various substituents, and their ionization energies and appearance energies, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 11, 2602. [all data]

Huisgen, Rapp, et al., 1954
Huisgen, R.; Rapp, W.; Ugi, I.; Walz, H.; Mergenthaler, E., Mittlere ringe II. Sterische hinderung der mesomerie in 1,2-benzo-cyclen-3-onen und verwandten verbindungen, Justus Liebigs Ann. Chem., 1954, 586, 1-29. [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