1,3,5-Cycloheptatriene

• Formula: C₇H₈
• Molecular weight: 92.1384
• IUPAC Standard InChI: InChI=1S/C7H8/c1-2-4-6-7-5-3-1/h1-6H,7H2 Copy

  
• IUPAC Standard InChIKey: CHVJITGCYZJHLR-UHFFFAOYSA-N Copy
• CAS Registry Number: 544-25-2
• 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: Tropilidene; Cyclohepta-1,3,5-triene; Cycloheptatriene; Tropilidin; UN 2603
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (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:
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

View reactions leading to C₇H₈⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₇^- +  =

By formula: C₇H₇^- + H⁺ = C₇H₈

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

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

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

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

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, custom temperature program

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

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References

Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

McCullough and Waddington, 1957
McCullough, J.P.; Waddington, G., Melting-point purity determinations: limitations as evidenced by calorimetric studies in the melting region, Anal. Chim. Acta, 1957, 17, 80. [all data]

Finke, Scott, et al., 1956
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, Cyclooctane and 1,3,5-Cycloheptatriene. Low Temperature Thermal Properties, Vapor Pressure and Derived Chemical Thermodynamic Prop., J. Am. Chem. Soc., 1956, 78, 5469. [all data]

Finke, Scott, et al., 1956, 2
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-54. [all data]

Finke, Scott, et al., 1956, 3
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-5476. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

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Kkykj, J.; Repas, M., Petrochemia, 1973, 13, 179. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Traeger and McLoughlin, 1978
Traeger, J.C.; McLoughlin, R.G., A photoionization study of the energetics of C₇H₇⁺ ion formed from C₇H₈ precursors, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 319. [all data]

Hoffman, 1974
Hoffman, M.K., Hidden rearrangements in the mass spectral decomposition of cycloheptatriene, Z. Naturforsch. A:, 1974, 29, 1077. [all data]

Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method, J. Am. Chem. Soc., 1970, 92, 19. [all data]

Akopyan and Vilesov, 1966
Akopyan, M.E.; Vilesov, F.I., A mass-spectrometric study of the photo-ionisation of benzene derivatives at wavelengths up to 885 A, Zh. Fiz. Khim., 1966, 40, 125, In original 63. [all data]

Price, Passmore, et al., 1963
Price, W.C.; Passmore, T.R.; Roessler, D.M., [Title unavailable], Faraday Discuss. Chem. Soc., 1963, 35, 238. [all data]

Muller, Schweig, et al., 1974
Muller, C.; Schweig, A.; Vermeer, H., Methode zur Berechnung induktiver und konjugativer Effekte - Andwendung auf Tropon, Angew. Chem., 1974, 86, 275. [all data]

Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F., The mass spectra of methyl-substituted cyclopentadienes, J. Am. Chem. Soc., 1965, 87, 5099. [all data]

Lifshitz and Bauer, 1963
Lifshitz, C.; Bauer, S.H., Mass spectra of valence tautomers, J. Phys. Chem., 1963, 67, 1629. [all data]

Traeger and McLoughlin, 1977
Traeger, J.C.; McLoughlin, R.G., Threshold photoionization and dissociation of toluene and cycloheptatriene, J. Am. Chem. Soc., 1977, 99, 7351. [all data]

Harrison, Honnen, et al., 1960
Harrison, A.G.; Honnen, L.R.; Dauben, H.J., Jr.; Lossing, F.P., Free radicals by mass spectrometry. XX. Ionization potentials of cyclopentadienyl and cycloheptatrienyl radicals, J. Am. Chem. Soc., 1960, 82, 5593. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Zhang, Chen, et al., 1997
Zhang, M.; Chen, B.; Shen, S.; Chen, S., Compositional studies of high-temperature coal tar by g.c.-FT-i.r. analysis of middle oil fractions, Fuel, 1997, 76, 5, 415-423, https://doi.org/10.1016/S0016-2361(97)85518-4 . [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]

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]

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]

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]

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]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J., Composition of the oil from waste tires. 2. Fraction boiling at 160-180 0C, Proc. Estonian Acad. Sci. Chem., 1999, 48, 3, 136-140. [all data]

Larsen and Frisvad, 1995
Larsen, T.O.; Frisvad, J.C., Characterization of volatile metabolites from 47 Penicillium taxa, Mycol. Res., 1995, 99, 10, 1153-1166, https://doi.org/10.1016/S0953-7562(09)80271-2 . [all data]

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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]

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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, 2
Robinson, P.G.; Odell, A.L., Comparison of isothermal and non-linear temperature programmed gas chromatography. The temperature dependence of the retention indices of a number of hydrocarbons on squalane and SE-30, J. Chromatogr., 1971, 57, 11-17, https://doi.org/10.1016/0021-9673(71)80002-X . [all data]

Tabanca, Kirimer, et al., 2001
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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, Phase change data, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  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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