1,3-Cyclohexadiene

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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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C6H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)837.kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity804.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.25PEKimura, Katsumata, et al., 1981LLK
8.25 ± 0.02PEBieri, Burger, et al., 1977LLK
8.25 ± 0.03PIDemeo and El-Sayed, 1970RDSH
8.25PEBischof and Heilbronner, 1970RDSH
8.28 ± 0.05EIFranklin and Carroll, 1969RDSH
8.32PEWorley, Webb, et al., 1979Vertical value; LLK
8.25 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H2+23.51 ± 0.50?EIFranklin and Carroll, 1969RDSH
C3H3+14.87 ± 0.10?EIFranklin and Carroll, 1969RDSH
C3H4+14.52 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+19.81 ± 0.10C2H2+2H2EIFranklin and Carroll, 1969RDSH
C4H3+17.62 ± 0.10C2H2+H2+H?EIFranklin and Carroll, 1969RDSH
C4H4+13.91 ± 0.20C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H5+14.69 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C4H6+12.60 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C5H3+15.44 ± 0.10CH3+H2?EIFranklin and Carroll, 1969RDSH
C5H5+13.02 ± 0.10CH3EIFranklin and Carroll, 1969RDSH
C6H5+13.92 ± 0.10H2+HEIFranklin and Carroll, 1969RDSH
C6H6+10.12 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C6H6+9.88 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C6H7+10.45HPIPECOLias and Ausloos, 1985LBLHLM
C6H7+10.82 ± 0.10HEIFranklin and Carroll, 1969RDSH

De-protonation reactions

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Δr1561. ± 17.kJ/molG+TSLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1531. ± 17.kJ/molIMRBLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B

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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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, 1990.
NIST MS number 118700

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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

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Column type Active phase Temperature (C) I Reference Comment
PackedC78, Branched paraffin130.689.6Dallos, Sisak, et al., 2000He; Column length: 3.3 m
PackedC78, Branched paraffin130.688.6Reddy, Dutoit, et al., 1992Chromosorb G HP; Column length: 3.3 m
PackedSqualane70.655.Safina, Poznyak, et al., 1989He, Risorb (0.2-0.3 mm); Column length: 2. m
CapillaryOV-1100.673.1Engewald, Billing, et al., 1987Column length: 50. m; Column diameter: 0.3 mm
CapillarySE-30130.684.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySE-3080.671.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillaryApiezon L100.693.Morishita, Okano, et al., 1980Column length: 45. m; Column diameter: 0.25 mm
CapillarySqualane50.652.8Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.653.4Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
PackedSqualane27.649.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane49.654.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane67.659.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane70.655.Bogoslovsky, Anvaer, et al., 1978 
PackedSqualane86.663.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane42.5652.Engewald, Epsch, et al., 1974N2; Column length: 100. m; Column diameter: 0.23 mm
CapillarySqualane70.655.Engewald, Epsch, et al., 1974N2; Column length: 100. m; Column diameter: 0.23 mm
PackedSE-3075.688.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m
PackedSqualane100.662.Robinson and Odell, 1971N2, Embacel; Column length: 3.0 m
PackedSqualane27.649.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.655.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.659.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.664.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
CapillarySqualane70.655.Schomburg, 1966 

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-20M100.883.Morishita, Okano, et al., 1980Column length: 75. m; Column diameter: 0.25 mm

Kovats' RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-Wax849.Umano and Shibamoto, 1987He, 40. C @ 10. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C

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

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Column type Active phase I Reference Comment
CapillaryPetrocol DH653.White, Hackett, et al., 1992100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C
PackedSE-30665.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, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
PackedSE-30665.Peng, Ding, et al., 1988Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min)

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

View large format table.

Column type Active phase I Reference Comment
PackedCarbowax 20M861.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, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane70.655.Schomburg, 1966, 2 

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH657.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryPONA634.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-101634.Orav, Kailas, et al., 199950. m/0.20 mm/0.50 μm, Helium, 30. C @ 6. min, 1. K/min; Tend: 100. C

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

View large format table.

Column type Active phase I Reference Comment
CapillarySqualane671.Chen, 2008Program: not specified
CapillaryOV-101664.Zenkevich, 1998He; Column length: 25. m; Column diameter: 0.20 mm; Program: not specified
CapillaryOV-101665.Zenkevich, 1998He; Column length: 25. m; Column diameter: 0.20 mm; Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.671.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
PackedSE-30678.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)
PackedSqualane692.Robinson and Odell, 1971N2, Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min => 35 => 4C/min => 95C(hold)

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax864.Peng, Yang, et al., 1991Program: not specified

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.

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [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]

Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E., Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen, Helv. Chim. Acta, 1970, 53, 1677. [all data]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., Effect of molecular structure on ionic decomposition. II. An electron-impact study of 1,3-and 1,4-cyclohexadiene and 1,3,5-hexatriene, J. Am. Chem. Soc., 1969, 91, 6564. [all data]

Worley, Webb, et al., 1979
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S., On the electronic structures of cyclobutadiene trimethylenemethane, J. Organomet. Chem., 1979, 168, 16. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Lias and Ausloos, 1985
Lias, S.G.; Ausloos, P., Structures of C6H7+ ions formed in unimolecular and bimolecular reactions, J. Chem. Phys., 1985, 82, 3613. [all data]

Lee and Squires, 1986
Lee, R.E.; Squires, R.R., Anionic homoaromaticity: A gas phase experimental study, J. Am. Chem. Soc., 1986, 105, 5078. [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Safina, Poznyak, et al., 1989
Safina, L.R.; Poznyak, T.I.; Lisitsyn, D.M.; Kiseleva, E.V.; Kovalev, G.I., Selective gas-chromatographic determination of trace unsaturated and aromatic-hydrocarbons in complex-mixtures, J. Appl. Chem. USSR (Engl. Transl.), 1989, 44, 5, 749-754. [all data]

Engewald, Billing, et al., 1987
Engewald, W.; Billing, U.; Welsch, T.; Haufe, G., Structure-retention correlations of hydrocarbons in gas-liquid and gas-solid chromatography. Cycloalkenes and cycloalkadienes, Chromatographia, 1987, 23, 8, 590-594, https://doi.org/10.1007/BF02324870 . [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]

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]

Engewald, Epsch, et al., 1974
Engewald, W.; Epsch, K.; Graefe, J.; Welsch, Th., Molekülstruktur und retentionsverhalten. II. Retentionsverhalten cycloaliphatischer kohlenwasser-stoffe bei der gas-adsorptions- und gas-verteilungschromatographie, J. Chromatogr., 1974, 91, 623-631, https://doi.org/10.1016/S0021-9673(01)97943-9 . [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]

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]

Umano and Shibamoto, 1987
Umano, K.; Shibamoto, T., Analysis of headspace volatiles from overheated beef fat, J. Agric. Food Chem., 1987, 35, 1, 14-18, https://doi.org/10.1021/jf00073a004 . [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]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Schomburg, 1966, 2
Schomburg, G., Gaschromatographische Retentionsdaten und Struktur Chemischer Verbindungen. II. Methylverzweigungen und Doppelbindungen in Offenkettigen Kohlenwasserstoffen, J. Chromatogr., 1966, 23, 1-17, https://doi.org/10.1016/S0021-9673(01)98652-2 . [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]

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, 1998
Zenkevich, I.G., Application of Methods of Molecular Dynamics in Chromato-Spectral Identification of ISomeric Products of Organic reactions (in Russian), Zh. Org. Khim., 1998, 34, 10, 1463-1470. [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]

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]


Notes

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