1,3,5,7-Cyclooctatetraene

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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 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 C8H8+ (ion structure unspecified)

Electron affinity determinations

EA (eV) Method Reference Comment
0.570 ± 0.030N/AMiller, Viggiano, et al., 2002B
0.550 ± 0.020IMREKato, Lee, et al., 1997B
0.650 ± 0.043LPESWenthold, Hrovat, et al., 1996EA(D4h COT) = 1.099 ± 0.01 eV. D4H is TS, 10-11 kcal/mol above GS D8h; B
0.58 ± 0.10CIDCDenault, Chen, et al., 1998entropy of attachment: -14.7±13 eu; B
<0.823919PDGygax, Peters, et al., 1979B
0.577 ± 0.043ECDWentworth and Ristau, 1969B

Ionization energy determinations

IE (eV) Method Reference Comment
8.03PEFu and Dunbar, 1978LLK
8.0PEBatich, Bischof, et al., 1973LLK
8.21PEDewar, Harget, et al., 1969Unpublished result of M.J.S. Dewar and S.D. Worley; RDSH
8.04PEAl-Joboury and Turner, 1964RDSH
7.99 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
8.43PEFu and Dunbar, 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.40 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+17.11 ± 0.102C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H3+18.16 ± 0.252C2H2+HEIFranklin and Carroll, 1969RDSH
C4H4+15.10 ± 0.102C2H2EIFranklin and Carroll, 1969RDSH
C5H3+16.41 ± 0.15C2H2+CH3?EIFranklin and Carroll, 1969RDSH
C6H5+14.58 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C6H6+9.4 ± 0.05C2H2TRPILifshitz and Malinovich, 1984LBLHLM
C6H6+9.70 ± 0.12C2H2EIFranklin and Carroll, 1969RDSH
C8H6+11.70 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C8H7+10.90 ± 0.10HEIFranklin and Carroll, 1969RDSH

De-protonation reactions

C8H7- + Hydrogen cation = 1,3,5,7-Cyclooctatetraene

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Δr382.7 ± 2.8kcal/molG+TSKato, Lee, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Δr374.8 ± 2.5kcal/molIMREKato, Lee, et al., 1997gas phase; B

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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NIST MS number 1259

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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
CapillarySqualane70.850.Schomburg, 1966 

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

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Column type Active phase I Reference Comment
PackedSE-30880.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

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Column type Active phase I Reference Comment
PackedSE-30880.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

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Column type Active phase I Reference Comment
CapillaryCarbowax 20M1244.Verzera, Campisi, et al., 200560. m/0.25 mm/0.25 μm, He, 45. C @ 0.17 min, 2. K/min; Tend: 250. C
CapillaryCP-Wax 52CB1244.Verzera, Campisi, et al., 200160. m/0.25 mm/0.25 μm, He, 45. C @ 0.17 min, 2. K/min; Tend: 250. C
CapillaryDB-Wax1264.Shimoda, Peralta, et al., 199660. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C
PackedCarbowax 20M1226.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

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Column type Active phase I Reference Comment
CapillaryCP Sil 8 CB894.Wang and Guo-Y. -L., 200430. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 10. K/min, 200. C @ 2. min

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

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Column type Active phase I Reference Comment
CapillarySqualane850.Chen, 2008Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.880.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
PackedSE-30889.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)
PackedSqualane846.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
CapillaryCarbowax 20M1244.Editorial paper, 2005Program: not specified
CapillaryDB-Wax1199.Peng, Yang, et al., 1991Program: not specified
CapillaryCarbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.1226.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: 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.

Miller, Viggiano, et al., 2002
Miller, T.M.; Viggiano, A.A.; Miller, A.E.S., Electron attachment and detachment: Cyclooctatetraene, J. Phys. Chem. A, 2002, 106, 43, 10200-10204, https://doi.org/10.1021/jp0205214 . [all data]

Kato, Lee, et al., 1997
Kato, S.; Lee, H.S.; Gareyev, R.; Wenthold, P.G.; Lineberger, W.C.; DePuy, C.H.; Bierbaum, V.M., Experimental and Computational Studies of the Structures and Energetics of Cyclooctatetraene and Its Derivatives, J. Am. Chem. Soc., 1997, 119, 33, 7863, https://doi.org/10.1021/ja971433d . [all data]

Wenthold, Hrovat, et al., 1996
Wenthold, P.G.; Hrovat, D.A.; Borden, W.T.; Lineberger, W.C., Transition State Spectroscopy of Cyclooctatetraene, Science, 1996, 272, 5267, 1456, https://doi.org/10.1126/science.272.5267.1456 . [all data]

Denault, Chen, et al., 1998
Denault, J.W.; Chen, G.D.; Cooks, R.G., Electron affinity of 1,3,5,7-cyclooctatetraene determined by the kinetic method, J. Am. Soc. Mass Spectrom., 1998, 9, 11, 1141-1145, https://doi.org/10.1016/S1044-0305(98)00092-0 . [all data]

Gygax, Peters, et al., 1979
Gygax, R.; Peters, H.L.; Brauman, J.I., Photodetachment of electrons from anions of high symmetry. Electron photodetachment spectra of the cycloctatetraenyl and perinaphthenyl anions, J. Am. Chem. Soc., 1979, 101, 2567. [all data]

Wentworth and Ristau, 1969
Wentworth, W.E.; Ristau, W., Thermal Electron Attachment Involving a Change in Molecular Geometry, J. Phys. Chem., 1969, 73, 7, 2126, https://doi.org/10.1021/j100727a005 . [all data]

Fu and Dunbar, 1978
Fu, E.W.; Dunbar, R.C., Photodissociation spectroscopy and structural rearrangements in ions of cyclooctatetraene, styrene and related molecules, J. Am. Chem. Soc., 1978, 100, 2283. [all data]

Batich, Bischof, et al., 1973
Batich, C.; Bischof, P.; Heilbronner, E., The photoelectron spectra of cyclooctatetraene and its hydrogenated derivatives, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 333. [all data]

Dewar, Harget, et al., 1969
Dewar, M.J.S.; Harget, A.; Haselbach, E., Cyclooctatetraene and ions derived from it, J. Am. Chem. Soc., 1969, 91, 7521. [all data]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [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]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., The effect of molecular structure on ionic decomposition. I. An electron impact study of seven C8H8 isomers, J. Am. Chem. Soc., 1969, 91, 5940. [all data]

Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y., Time resolved photoionization mass spectrometry in the millisecond range, Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [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]

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]

Verzera, Campisi, et al., 2005
Verzera, A.; Campisi, S.; Zappalá, M., SUPELCO. Using SPME-GC-MS to characterize volatile components of honey as indicators of botanical origin, 2005, retrieved from http://www.sigmaaldrich.com/Brands/SupelcoHome/TheReporter.html. [all data]

Verzera, Campisi, et al., 2001
Verzera, A.; Campisi, S.; Zappalá, M.; Bonaccorsi, I., SPME-GC-MS analysis of honey volatile components for the characterization of different floral origin, Am. Lab. Fairfield Conn., 2001, 33, 15, 18-21. [all data]

Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y., Headspace gas analysis of fish sauce, J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u . [all data]

Wang and Guo-Y. -L., 2004
Wang, H.-Y.; Guo-Y. -L., Rapid analysis of the volatile compounds in the rhizomes of Rhodiola sachalinensis and Rhodiola sacra by static headspace-gas chromatography-tandem mass spectrometry, Anal. Letters, 2004, 37, 10, 2151-2161, https://doi.org/10.1081/AL-200026690 . [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]

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]

Editorial paper, 2005
Editorial paper, Solid Phase Microextraction (SPME) Application Guide, The Reporter Europe (Supelco), 2005, 16, 5, 12-12. [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