Cyclohexane, methylene-

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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
Δcliquid-4412.4kJ/molCcbKonovalon, 1926Heat of combustion at 15°C; Corresponding Δfliquid = -56.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
177.4298.15Fuchs and Peacock, 1979DH

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil377. ± 4.KAVGN/AAverage of 20 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus168.430KN/AStreiff, 1964Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; TRC
Tfus168.440KN/AStreiff, 1964Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Tfus166.5KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Δvap36.1 ± 0.3kJ/molCFuchs and Peacock, 1979ALS
Δvap36.1 ± 0.3kJ/molGCCFuchs and Peacock, 1979AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
34.4346.A,EBStephenson and Malanowski, 1987Based on data from 331. to 387. K. See also Meyer and Hotz, 1973.; AC

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:


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 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C7H12+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.8PELambert, Xue, et al., 1986LBLHLM
8.93 ± 0.01PESarneel, Worrell, et al., 1980LLK
9.7EIShikhmamedbekova, Aslanov, et al., 1970RDSH
8.94PEDemeo and Yencha, 1970RDSH
8.97 ± 0.01PIDemeo and El-Sayed, 1970RDSH
9.04 ± 0.03EIWinters and Collins, 1968RDSH
9.13PESpanka and Rademacher, 1986Vertical value; LBLHLM
9.18PELambert, Xue, et al., 1986Vertical value; LBLHLM
9.08 ± 0.01PESarneel, Worrell, et al., 1980Vertical value; LLK
9.12 ± 0.02PEMartin, Heller, et al., 1974Vertical value; LLK
9.13PEAsmus and Klessinger, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.90 ± 0.13?EIWinters and Collins, 1968RDSH
C3H5+13.25 ± 0.11?EIWinters and Collins, 1968RDSH
C4H5+13.10 ± 0.10?EIWinters and Collins, 1968RDSH
C4H6+13.2C3H6EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C4H6+10.94 ± 0.05?EIWinters and Collins, 1968RDSH
C4H7+13.7C3H5EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C4H7+11.34 ± 0.04?EIWinters and Collins, 1968RDSH
C5H7+12.5C2H5EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C5H7+10.45 ± 0.11C2H5EIWinters and Collins, 1968RDSH
C5H8+12.2C2H4EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C5H8+10.46 ± 0.08C2H4EIWinters and Collins, 1968RDSH
C6H8+11.2CH4EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C6H9+10.27 ± 0.08CH3EIWinters and Collins, 1968RDSH
C6H10+11.7CH2EIShikhmamedbekova, Aslanov, et al., 1970RDSH

References

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

Konovalon, 1926
Konovalon, D.-P., Sur Les Chaleurs de Combustion de Quelques hydrocarbures cycliques, J. Chim. Phys., 1926, 23, 359-362. [all data]

Fuchs and Peacock, 1979
Fuchs, R.; Peacock, L.A., Heats of vaporization and gaseous heats of formation of some five- and six-membered ring alkenes, Can. J. Chem., 1979, 57, 2302-2304. [all data]

Streiff, 1964
Streiff, A.J., , Am. Pet. Inst. Res. Proj. 58B Unpublished, 1964. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [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]

Lambert, Xue, et al., 1986
Lambert, J.B.; Xue, L.; Bosch, R.J.; Taba, K.M.; Marko, D.E.; Urano, S.; LeBreton, P.R., Through space interactions of double bonds by photoelectron spectroscopy, J. Am. Chem. Soc., 1986, 108, 7575. [all data]

Sarneel, Worrell, et al., 1980
Sarneel, R.; Worrell, C.W.; Pasman, P.; Verhoeven, J.W.; Mes, G.F., The photoelectron spectra of 4-methylene thiacyclohexane derivatives through-bond interaction, Tetrahedron, 1980, 36, 3241. [all data]

Shikhmamedbekova, Aslanov, et al., 1970
Shikhmamedbekova, A.Z.; Aslanov, F.A.; Gadzhiev, M.M.; Gulamova, T.E.; Akhmedova, F.N., Mass spectrometric study of methylene cycloalkenes, Dokl. Phys. Chem., 1970, 26, 34. [all data]

Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J., Photoelectron spectra of bicyclic and exocyclic olefins, J. Chem. Phys., 1970, 53, 4536. [all data]

Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A., Ionization potential and structure of olefins, J. Chem. Phys., 1970, 52, 2622. [all data]

Winters and Collins, 1968
Winters, R.E.; Collins, J.H., Mass spectrometric studies of structural isomers. I. Mono- and bicyclic C7H12 molecules, J. Am. Chem. Soc., 1968, 90, 1235. [all data]

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

Martin, Heller, et al., 1974
Martin, H.-D.; Heller, C.; Werp, J., Bishomofulvenkonjugation. Photoelektronenspektren und elektronenstruktur homologer quadricyclane, Chem. Ber., 1974, 107, 1393. [all data]

Asmus and Klessinger, 1974
Asmus, P.; Klessinger, M., Photoelectron spectra of organic compounds. VI. Exocyclic methylene compounds, Tetrahedron, 1974, 30, 2477. [all data]


Notes

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