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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
Deltacliquid-4412.4kJ/molCcbKonovalon, 1926Heat of combustion at 15°C; Corresponding «DELTA»fliquid = -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
Deltavap36.1 ± 0.3kJ/molCFuchs and Peacock, 1979ALS
Deltavap36.1 ± 0.3kJ/molGCCFuchs and Peacock, 1979AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
34.4346.A,EBStephenson and Malanowski, 1987Based on data from 331. - 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:


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 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

Cyclohexane, methylene- + Hydrogen = Cyclohexane, methyl-

By formula: C7H12 + H2 = C7H14

Quantity Value Units Method Reference Comment
Deltar-119.5 ± 0.65kJ/molChydRogers, Crooks, et al., 1987liquid phase
Deltar-116.1 ± 0.54kJ/molChydTurner and Garner, 1958liquid phase; solvent: Acetic acid
Deltar-116.1 ± 0.54kJ/molEqkTurner and Garner, 1957liquid phase; solvent: Acetic acid
Deltar-120.1 ± 0.3kJ/molChydTurner and Garner, 1957, 2liquid phase; solvent: Acetic acid

Cyclohexane, methylene- + Trifluoroacetic acid = Acetic acid, trifluoro-, 1-methyl cyclohexyl ester

By formula: C7H12 + C2HF3O2 = C9H13F3O3

Quantity Value Units Method Reference Comment
Deltar-44.81 ± 0.10kJ/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis

Cyclohexane, methylene- = Cyclohexene, 1-methyl-

By formula: C7H12 = C7H12

Quantity Value Units Method Reference Comment
Deltar-7.2 ± 0.3kJ/molEqkYursha, Kabo, et al., 1974gas phase; Heat of isomerization at 463 K

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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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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

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 Japan AIST/NIMC Database- Spectrum MS-NW-3425
NIST MS number 235403

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
CapillaryOV-101100.750.Diez, Guillen, et al., 1990N2; Column length: 25. m; Column diameter: 0.23 mm
CapillaryOV-10180.744.Diez, Guillen, et al., 1990N2; Column length: 25. m; Column diameter: 0.23 mm
CapillarySqualane100.743.Diez, Guillen, et al., 1990N2; Column length: 45. m; Column diameter: 0.5 mm
CapillarySqualane80.737.8Diez, Guillen, et al., 1990N2; Column length: 45. m; Column diameter: 0.5 mm
CapillarySE-54100.759.3Diez, Guillen, et al., 1990N2; Column length: 25. m; Column diameter: 0.22 mm
CapillarySE-5480.754.1Diez, Guillen, et al., 1990N2; Column length: 25. m; Column diameter: 0.22 mm
CapillaryBP-1100.750.Bermejo, Blanco, et al., 1987N2; Column length: 12. m; Column diameter: 0.22 mm
CapillaryBP-180.745.Bermejo, Blanco, et al., 1987N2; Column length: 12. m; Column diameter: 0.22 mm
CapillaryOV-101100.750.Bermejo, Blanco, et al., 1987N2; Column length: 25. m; Column diameter: 0.23 mm
CapillaryOV-10180.744.Bermejo, Blanco, et al., 1987N2; Column length: 25. m; Column diameter: 0.23 mm
CapillaryOV-1100.750.8Anders, Anders, et al., 198555. m/0.21 mm/0.35 «mu»m, N2
CapillarySE-30130.758.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySE-3080.745.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySE-3080.745.5Albaigés and Guardino, 1980He; Column length: 64. m; Column diameter: 0.25 mm
CapillarySqualane80.737.5Albaigés and Guardino, 1980He; Column length: 100. m; Column diameter: 0.25 mm
PackedSqualane27.726.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.732.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.736.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.741.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
CapillarySqualane70.736.Schomburg, 1966 

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5741.7Xu, van Stee, et al., 200330. m/0.25 mm/1. «mu»m, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C
CapillaryPetrocol DH731.White, Hackett, et al., 1992100. m/0.25 mm/0.5 «mu»m, He, 1. K/min; Tstart: 30. C; Tend: 220. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5 MS750.Kim and Chung, 200930. m/0.25 mm/0.25 «mu»m, Helium, 35. C @ 5. min, 2. K/min, 195. C @ 30. min

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

View large format table.

Column type Active phase I Reference Comment
CapillarySqualane738.Chen, 2008Program: not specified
CapillarySqualane745.Chen, 2008Program: not specified
CapillaryMethyl Silicone739.Zenkevich, 2000Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.745.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

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]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215. [all data]

Turner and Garner, 1958
Turner, R.B.; Garner, R.H., Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs, J. Am. Chem. Soc., 1958, 80, 1424-1430. [all data]

Turner and Garner, 1957
Turner, R.B.; Garner, R.H., Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs, J. Am. Chem. Soc., 1957, 80, 1424-1430. [all data]

Turner and Garner, 1957, 2
Turner, R.B.; Garner, R.H., The stability relationship of 1-methyl-cyclopentene and methylenecyclopentane, J. Am. Chem. Soc., 1957, 79, 253. [all data]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]

Yursha, Kabo, et al., 1974
Yursha, I.A.; Kabo, G.Ya.; Andreevskii, D.N., Equilibriums and thermodynamics of the isomerization of methylcyclohexenes, Neftekhimiya, 1974, 14, 688-693. [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/«pi» 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]

Diez, Guillen, et al., 1990
Diez, M.A.; Guillen, M.D.; Blanco, C.G.; Bermejo, J., Chromatographic study of methylcyclopentadiene dimers and iso-dimers and determination of their boiling points, J. Chromatogr., 1990, 508, 363-374, https://doi.org/10.1016/S0021-9673(00)91279-2 . [all data]

Bermejo, Blanco, et al., 1987
Bermejo, J.; Blanco, C.G.; Diez, M.A.; Guillén, M.D., Kováts retention indices of selected mono and polycyclic olefins, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1987, 10, 8, 461-463, https://doi.org/10.1002/jhrc.1240100809 . [all data]

Anders, Anders, et al., 1985
Anders, G.; Anders, K.; Engewald, W., Identification of non-branched alkenylcycloalkanes with a terminal double bond from retention index increments, Chromatographia, 1985, 20, 2, 83-86, https://doi.org/10.1007/BF02280602 . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Albaigés and Guardino, 1980
Albaigés, J.; Guardino, X., Gas chromatographic-mass spectrometric identification of alkylcyclohexanes and cyclohexenes, Chromatographia, 1980, 13, 12, 755-762, https://doi.org/10.1007/BF02265555 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe, J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4 . [all data]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Kim and Chung, 2009
Kim, J.-S.; Chung, H.Y., GC-MS analysis of the volatile components in dried boxthorn (Lycium chimensis) Fruit, J. Korean Soc. Appl. Biol. Chem., 2009, 52, 5, 516-524, https://doi.org/10.3839/jksabc.2009.088 . [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Zenkevich, 2000
Zenkevich, I.G., Mutual Correlation between Gas Chromatographic Retention Indices of Unsaturated and Saturated Hydrocarbons found by Molecular Dynamics, Z. Anal. Chem., 2000, 55, 10, 1091-1097. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References