Cyclohexane, methylene-
- Formula: C7H12
- Molecular weight: 96.1702
- IUPAC Standard InChIKey: YULMNMJFAZWLLN-UHFFFAOYSA-N
- CAS Registry Number: 1192-37-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Methylenecyclohexane; 1-Methylenecyclohexane
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Phase change data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
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 |
---|---|---|---|---|---|
Tboil | 377. ± 4. | K | AVG | N/A | Average of 20 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 168.430 | K | N/A | Streiff, 1964 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; TRC |
Tfus | 168.440 | K | N/A | Streiff, 1964 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 166.5 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 36.1 ± 0.3 | kJ/mol | C | Fuchs and Peacock, 1979 | ALS |
ΔvapH° | 36.1 ± 0.3 | kJ/mol | GCC | Fuchs and Peacock, 1979 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.4 | 346. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 331. to 387. K. See also Meyer and Hotz, 1973.; AC |
Reaction thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
By formula: C7H12 + H2 = C7H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -119.5 ± 0.65 | kJ/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
ΔrH° | -116.1 ± 0.54 | kJ/mol | Chyd | Turner and Garner, 1958 | liquid phase; solvent: Acetic acid |
ΔrH° | -116.1 ± 0.54 | kJ/mol | Eqk | Turner and Garner, 1957 | liquid phase; solvent: Acetic acid |
ΔrH° | -120.1 ± 0.3 | kJ/mol | Chyd | Turner and Garner, 1957, 2 | liquid phase; solvent: Acetic acid |
By formula: C7H12 + C2HF3O2 = C9H13F3O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -44.81 ± 0.10 | kJ/mol | Cac | Wiberg, Wasserman, et al., 1985 | liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis |
By formula: C7H12 = C7H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.2 ± 0.3 | kJ/mol | Eqk | Yursha, Kabo, et al., 1974 | gas phase; Heat of isomerization at 463 K |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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 |
---|---|---|---|
8.8 | PE | Lambert, Xue, et al., 1986 | LBLHLM |
8.93 ± 0.01 | PE | Sarneel, Worrell, et al., 1980 | LLK |
9.7 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
8.94 | PE | Demeo and Yencha, 1970 | RDSH |
8.97 ± 0.01 | PI | Demeo and El-Sayed, 1970 | RDSH |
9.04 ± 0.03 | EI | Winters and Collins, 1968 | RDSH |
9.13 | PE | Spanka and Rademacher, 1986 | Vertical value; LBLHLM |
9.18 | PE | Lambert, Xue, et al., 1986 | Vertical value; LBLHLM |
9.08 ± 0.01 | PE | Sarneel, Worrell, et al., 1980 | Vertical value; LLK |
9.12 ± 0.02 | PE | Martin, Heller, et al., 1974 | Vertical value; LLK |
9.13 | PE | Asmus and Klessinger, 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 13.90 ± 0.13 | ? | EI | Winters and Collins, 1968 | RDSH |
C3H5+ | 13.25 ± 0.11 | ? | EI | Winters and Collins, 1968 | RDSH |
C4H5+ | 13.10 ± 0.10 | ? | EI | Winters and Collins, 1968 | RDSH |
C4H6+ | 13.2 | C3H6 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
C4H6+ | 10.94 ± 0.05 | ? | EI | Winters and Collins, 1968 | RDSH |
C4H7+ | 13.7 | C3H5 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
C4H7+ | 11.34 ± 0.04 | ? | EI | Winters and Collins, 1968 | RDSH |
C5H7+ | 12.5 | C2H5 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
C5H7+ | 10.45 ± 0.11 | C2H5 | EI | Winters and Collins, 1968 | RDSH |
C5H8+ | 12.2 | C2H4 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
C5H8+ | 10.46 ± 0.08 | C2H4 | EI | Winters and Collins, 1968 | RDSH |
C6H8+ | 11.2 | CH4 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
C6H9+ | 10.27 ± 0.08 | CH3 | EI | Winters and Collins, 1968 | RDSH |
C6H10+ | 11.7 | CH2 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
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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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 |
Gas Chromatography
Go To: Top, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 100. | 750. | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 80. | 744. | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | Squalane | 100. | 743. | Diez, Guillen, et al., 1990 | N2; Column length: 45. m; Column diameter: 0.5 mm |
Capillary | Squalane | 80. | 737.8 | Diez, Guillen, et al., 1990 | N2; Column length: 45. m; Column diameter: 0.5 mm |
Capillary | SE-54 | 100. | 759.3 | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | SE-54 | 80. | 754.1 | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | BP-1 | 100. | 750. | Bermejo, Blanco, et al., 1987 | N2; Column length: 12. m; Column diameter: 0.22 mm |
Capillary | BP-1 | 80. | 745. | Bermejo, Blanco, et al., 1987 | N2; Column length: 12. m; Column diameter: 0.22 mm |
Capillary | OV-101 | 100. | 750. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 80. | 744. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | OV-1 | 100. | 750.8 | Anders, Anders, et al., 1985 | 55. m/0.21 mm/0.35 μm, N2 |
Capillary | SE-30 | 130. | 758. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 80. | 745. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 80. | 745.5 | Albaigés and Guardino, 1980 | He; Column length: 64. m; Column diameter: 0.25 mm |
Capillary | Squalane | 80. | 737.5 | Albaigés and Guardino, 1980 | He; Column length: 100. m; Column diameter: 0.25 mm |
Packed | Squalane | 27. | 726. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 732. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 736. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 741. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 736. | Schomburg, 1966 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 741.7 | Xu, van Stee, et al., 2003 | 30. m/0.25 mm/1. μm, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C |
Capillary | Petrocol DH | 731. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 750. | Kim and Chung, 2009 | 30. m/0.25 mm/0.25 μm, Helium, 35. C @ 5. min, 2. K/min, 195. C @ 30. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 738. | Chen, 2008 | Program: not specified |
Capillary | Squalane | 745. | Chen, 2008 | Program: not specified |
Capillary | Methyl Silicone | 739. | Zenkevich, 2000 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 745. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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/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]
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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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