Cyclohexene, 4-methyl-

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Gas phase ion energetics data

Go To: Top, 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C7H12+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.91 ± 0.01PERang, Paldoia, et al., 1974LLK
8.92EIWinters and Collins, 1968RDSH
8.91 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+14.02 ± 0.15?EIWinters and Collins, 1968RDSH
C3H5+13.38 ± 0.11?EIWinters and Collins, 1968RDSH
C4H5+13.43 ± 0.13?EIWinters and Collins, 1968RDSH
C4H6+10.82 ± 0.12?EIWinters and Collins, 1968RDSH
C4H7+11.24 ± 0.04?EIWinters and Collins, 1968RDSH
C5H7+10.43 ± 0.10C2H5EIWinters and Collins, 1968RDSH
C5H8+10.39 ± 0.05C2H4EIWinters and Collins, 1968RDSH
C6H9+10.16CH3EILossing and Holmes, 1984LBLHLM
C6H9+10.12 ± 0.10CH3EIWinters and Collins, 1968RDSH

Mass spectrum (electron ionization)

Go To: Top, Gas phase ion energetics data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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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-4941
NIST MS number 227868

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Gas Chromatography

Go To: Top, Gas phase ion energetics data, 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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-101100.748.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
CapillarySqualane100.744.6Diez, Guillen, et al., 1990N2; Column length: 45. m; Column diameter: 0.5 mm
CapillarySqualane80.739.9Diez, Guillen, et al., 1990N2; Column length: 45. m; Column diameter: 0.5 mm
CapillarySE-54100.757.5Diez, Guillen, et al., 1990N2; Column length: 25. m; Column diameter: 0.22 mm
CapillarySE-5480.751.2Diez, Guillen, et al., 1990N2; Column length: 25. m; Column diameter: 0.22 mm
CapillaryBP-1100.749.Bermejo, Blanco, et al., 1987N2; Column length: 12. m; Column diameter: 0.22 mm
CapillaryBP-180.744.Bermejo, Blanco, et al., 1987N2; Column length: 12. m; Column diameter: 0.22 mm
CapillaryOV-101100.748.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
CapillaryDB-140.733.Lubeck and Sutton, 198460. m/0.264 mm/0.25 μm, H2
CapillaryHP-PONA40.733.Lubeck and Sutton, 198450. m/0.21 mm/0.5 μm, H2
CapillarySE-30130.754.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySE-3080.743.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySE-3080.742.8Albaigés and Guardino, 1980He; Column length: 64. m; Column diameter: 0.25 mm
CapillarySqualane80.739.5Albaigés and Guardino, 1980He; Column length: 100. m; Column diameter: 0.25 mm
CapillaryApiezon L100.766.Morishita, Okano, et al., 1980Column length: 45. m; Column diameter: 0.25 mm
CapillarySqualane50.733.2Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.738.1Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
PackedSqualane30.728.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane50.734.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane60.739.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane70.742.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane80.743.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane100.746.Rang, Orav, et al., 1977Nitrogen or helium; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane100.739.1Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane100.742.Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane100.745.5Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane100.747.1Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane100.749.Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane55.747.1Lulova, Leont'eva, et al., 1975He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane55.749.Lulova, Leont'eva, et al., 1975He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane30.729.6Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane60.736.3Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane80.741.8Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane30.730.Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane60.736.Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane80.742.Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
PackedSqualane27.728.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.734.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.738.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.744.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
CapillarySqualane70.739.Schomburg, 1966 

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG 4000100.893.Rang, Orav, et al., 1988 
CapillaryPEG 400060.874.Rang, Orav, et al., 1988 
CapillaryPEG 400080.884.Rang, Orav, et al., 1988 
CapillaryPEG-20M80.883.Rang, Orav, et al., 1988 
CapillaryPEG-20M100.869.Morishita, Okano, et al., 1980Column length: 75. m; Column diameter: 0.25 mm
CapillaryPEG 4000100.893.Rang, Orav, et al., 1977Nitrogen or Helium; Column length: 45. m; Column diameter: 0.25 mm
CapillaryPolyethylene Glycol 4000100.893.1Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPolyethylene Glycol 400060.874.0Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPolyethylene Glycol 400080.883.9Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPEG 4000100.893.1Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPEG 400060.874.Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPEG 400080.883.9Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm

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

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH729.8White, Douglas, et al., 1992100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C
CapillaryPetrocol DH729.83White, Douglas, et al., 1992100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C
CapillaryPetrocol DH730.White, Hackett, et al., 1992100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C
PackedSE-30744.Buchman, Cao, et al., 1984He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m

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

View large format table.

Column type Active phase I Reference Comment
PackedCarbowax 20M849.Buchman, Cao, et al., 1984He, Supelcoport, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH733.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryPetrocol DH735.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryPONA737.Zhang, Ding, et al., 200950. m/0.20 mm/0.50 μm, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min
CapillaryOV-101734.Orav, Kailas, et al., 199950. m/0.20 mm/0.50 μm, Helium, 30. C @ 6. min, 1. K/min; Tend: 100. C
CapillaryOV-101740.Chupalov and Zenkevich, 1996N2, 3. K/min; Column length: 52. m; Column diameter: 0.26 mm; Tstart: 50. C; Tend: 220. C
PackedApiezon L715.Dahlmann, Köser, et al., 1979Chromosorb G-AW-DMCS, 10. K/min; Column length: 2. m; Tstart: 25. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone740.Zenkevich, 2000Program: not specified
CapillaryPolydimethyl siloxanes740.Zenkevich, Chupalov, et al., 1996Program: not specified
CapillaryDB-1728.Ciccioli, Cecinato, et al., 199460. m/0.32 mm/0.25 μm; Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.744.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
PackedSE-30751.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax859.Peng, Yang, et al., 1991Program: not specified

Lee's RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-595.6Donnelly, Abdel-Hamid, et al., 199330. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min

References

Go To: Top, Gas phase ion energetics data, 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.

Rang, Paldoia, et al., 1974
Rang, S.; Paldoia, P.; Talvari, A., Ionization potentials of unsaturated hydrocarbons. 2. Mono-substituted cyclopentenes and cyclohexenes, Eesti. NSV Tead. Akad. Toim., 1974, 354. [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]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Lossing and Holmes, 1984
Lossing, F.P.; Holmes, J.L., Stabilization energy and ion size in carbocations in the gas phase, J. Am. Chem. Soc., 1984, 106, 6917. [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]

Lubeck and Sutton, 1984
Lubeck, A.J.; Sutton, D.L., Kovats Retention Indices of Selected Olefins on Bonded Phase Fused Silica Capillaries, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1984, 7, 9, 542-544, https://doi.org/10.1002/jhrc.1240070913 . [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]

Morishita, Okano, et al., 1980
Morishita, F.; Okano, T.; Kojima, T., Retention indices of monocyclic monoterpene hydrocarbons, Bunseki Kagaku, 1980, 29, 1, 48-53, https://doi.org/10.2116/bunsekikagaku.29.48 . [all data]

Bajus, Veselý, et al., 1979
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 2. Pyrolysis of methylcyclohexane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 2, 135-142, https://doi.org/10.1021/i360070a012 . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Rang, Orav, et al., 1977
Rang, S.; Orav, A.; Kuningas, K.; Eisen, O., Capillary Gas Chromatography of Monosubstituted Cyclopentenes and Cyclohexenes, Chromatographia, 1977, 10, 3, 115-122, https://doi.org/10.1007/BF02297862 . [all data]

Lulova, Leont'eva, et al., 1976
Lulova, N.I.; Leont'eva, S.A.; Timofeeva, A.N., Gas-chromatographic method of determination of individual hydrocarbons in catalytic cracking gasolines in Proceedings of All-Union Research Institute on Oil Processes. Vol.18, All-Union Research Institute on Oil Processes, Moscow, 1976, 30-53. [all data]

Lulova, Leont'eva, et al., 1975
Lulova, N.I.; Leont'eva, S.A.; Fedosova, A.K.; Kvasova, V.A., Individual composition of hydrocarbons in naphthas from secondary processes, Chem. Technol. Fuels Oils (Engl. Transl.), 1975, 11, 1/2, 59-64, https://doi.org/10.1007/BF00717315 . [all data]

Eisen, Orav, et al., 1972
Eisen, O.; Orav, A.; Rang, S., Identifizierung von Normal-Alkenen, Cyclopentenen und -Hexenen mittels Kapillar-Gas-Chromatographie. Identification des alcènes, cyclopentènes et -hexènes à l'aide de la chromatogrpahie en phase gazeuse sur colonne capillaire, Chromatographia, 1972, 5, 11, 229-239, https://doi.org/10.1007/BF02270600 . [all data]

Orav and Eisen, 1972
Orav, A.; Eisen, O., The retention indexes for alkenes, alkynes and cyclenes on capillary columns, Izv. Akad. Nauk Est. SSR, Khim. Geol., 1972, 21, 1, 39-47. [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]

Rang, Orav, et al., 1988
Rang, S.A.; Orav, A.E.; Kuningas, K.R.; Meister, A.E.; Strense, T.V.; Eisen, O.G., Gas-Chromatographic Characteristics of unsaturated hydrocarbons, Academy of Sciences of Estonia SSR, Tallinn, Estonia SSR, 1988, 208. [all data]

White, Douglas, et al., 1992
White, C.M.; Douglas, L.J.; Hackett, J.P.; Anderson, R.R., Characterization of synthetic gasoline from the chloromethane-zeolite reaction, Energy Fuels, 1992, 6, 1, 76-82, https://doi.org/10.1021/ef00031a012 . [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]

Buchman, Cao, et al., 1984
Buchman, O.; Cao, G.-Y.; Peng, C.T., Structure assignment by retention index in gas-liquid radiochromatography of substituted cyclohexenes, J. Chromatogr., 1984, 312, 75-90, https://doi.org/10.1016/S0021-9673(01)92765-7 . [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]

Zhang, Ding, et al., 2009
Zhang, X.; Ding, L.; Sun, Z.; Song, L.; Sun, T., Study on quantitative structure-retention relationships for hydrocarbons in FCC gasoline, Chromatographia, 2009, 70, 3/4, 511-518, https://doi.org/10.1365/s10337-009-1174-0 . [all data]

Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J., Composition of the oil from waste tires. 1. Fraction boiling at yp to 160 0C, Proc. Estonian Acad. Sci. Chem., 1999, 48, 1, 30-39. [all data]

Chupalov and Zenkevich, 1996
Chupalov, A.A.; Zenkevich, I.G., Chromatographic Characterization of Structural Transformations of Organic Compounds in Diels-Alder Reaction. Aliphatic Dienes and Dienophyls, Zh. Org. Khim., 1996, 32, 6, 675-684. [all data]

Dahlmann, Köser, et al., 1979
Dahlmann, G.; Köser, H.J.K.; Oelert, H.H., Multiple korrelation von retentionsindizes, Chromatographia, 1979, 12, 10, 665-671, https://doi.org/10.1007/BF02302943 . [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]

Zenkevich, Chupalov, et al., 1996
Zenkevich, I.G.; Chupalov, A.A.; Herzschuh, R., Correlation of the Increments of Gas Chromatographic Retention Indices with the Differences of Innermolecular Energies of Reagents and Products of Chemical Reactions, Zh. Org. Khim. (Rus.), 1996, 32, 11, 1685-1691. [all data]

Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R., Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas, Eur Commission EUR, 1994, 549-568. [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]

Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L., A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices, J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F., Application of gas chromatographic retention properties to the identification of environmental contaminants, J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I . [all data]


Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References