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
IUPAC Standard InChIKey: CHVJITGCYZJHLR-UHFFFAOYSA-N
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
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Other data available:
Data at other public NIST sites:
- Microwave spectra (on physics lab web site)
- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	187.	kJ/mol	Chyd	Roth, Bohm, et al., 1983	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	315.6 ± 1.1	J/mol*K	N/A	Finke H.L., 1956	GT

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
33.95	50.	Dorofeeva O.V., 1986	Recommended S(298.15 K) value agrees with experimental value within its uncertainty. Value of S(298.15 K) calculated by [ Evans M.V., 1960] is 2.4 J/mol*K larger than experimental one.; GT
42.24	100.
55.52	150.
71.04	200.
96.97	273.15
106.3 ± 3.5	298.15
106.94	300.
142.80	400.
173.73	500.
199.18	600.
220.09	700.
237.49	800.
252.14	900.
264.56	1000.
275.16	1100.
284.24	1200.
292.05	1300.
298.79	1400.
304.63	1500.

Reaction thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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

3 + 1,3,5-Cycloheptatriene =

By formula: 3H₂ + C₇H₈ = C₇H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-305. ± 0.4	kJ/mol	Chyd	Roth, Klaerner, et al., 1983	liquid phase; solvent: Isooctane; ALS
Δ_rH°	-294.9 ± 1.6	kJ/mol	Chyd	Turner, Meador, et al., 1957	liquid phase; solvent: Acetic acid; ALS
Δ_rH°	-301.7 ± 1.3	kJ/mol	Chyd	Conn, Kistiakowsky, et al., 1939	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -304.8 ± 0.04 kJ/mol; at 355 K; ALS

C₇H₇^- + = 1,3,5-Cycloheptatriene

By formula: C₇H₇^- + H⁺ = C₇H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1570. ± 9.2	kJ/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1545. ± 8.4	kJ/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B

= 1,3,5-Cycloheptatriene

By formula: C₇H₈ = C₇H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	0.669	kJ/mol	Eqk	Gorlitz and Gunther, 1969	liquid phase; NMR; ALS

Gas phase ion energetics data

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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

IE (eV)	Method	Reference	Comment
8.29	PI	Traeger and McLoughlin, 1978	LLK
8.03	PE	Traeger and McLoughlin, 1978	LLK
8.52	EI	Hoffman, 1974	LLK
8.40	PE	Bodor, Dewar, et al., 1970	RDSH
8.20 ± 0.05	PI	Akopyan and Vilesov, 1966	RDSH
8.28	S	Price, Passmore, et al., 1963	RDSH
8.50	PE	Muller, Schweig, et al., 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₅H₅⁺	16.66	?	EI	Harrison, Haynes, et al., 1965	RDSH
C₅H₅⁺	16.0	?	EI	Lifshitz and Bauer, 1963	RDSH
C₆H₅⁺	14.17	CH₃	EI	Hoffman, 1974	LLK
C₇H₇⁺	9.36	H	PI	Traeger and McLoughlin, 1978	LLK
C₇H₇⁺	9.36 ± 0.02	H	TE	Traeger and McLoughlin, 1977	LLK
C₇H₇⁺	10.73	H	EI	Hoffman, 1974	LLK
C₇H₇⁺	≤10.0	H	PI	Akopyan and Vilesov, 1966	RDSH
C₇H₇⁺	10.1 ± 0.2	H	EI	Harrison, Honnen, et al., 1960	RDSH

De-protonation reactions

C₇H₇^- + = 1,3,5-Cycloheptatriene

By formula: C₇H₇^- + H⁺ = C₇H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1570. ± 9.2	kJ/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1545. ± 8.4	kJ/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B

Gas Chromatography

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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
Capillary	OV-1	150.	807.	Zhang, Chen, et al., 1997	25. m/0.2 mm/0.33 μm, N2
Capillary	OV-1	150.	794.	Zhang, Chen, et al., 1997	25. m/0.2 mm/0.33 μm, N2
Capillary	SE-30	130.	800.	Bredael, 1982	Column length: 100. m; Column diameter: 0.5 mm
Capillary	SE-30	80.	784.	Bredael, 1982	Column length: 100. m; Column diameter: 0.5 mm
Capillary	Squalane	50.	782.6	Bajus, Veselý, et al., 1979	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	70.	786.6	Bajus, Veselý, et al., 1979	Column length: 100. m; Column diameter: 0.25 mm
Packed	Squalane	100.	774.	Robinson and Odell, 1971	N2, Embacel; Column length: 3.0 m
Packed	Squalane	27.	756.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	49.	763.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	67.	769.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	86.	775.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. 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
Capillary	Petrocol DH	771.	White, Hackett, et al., 1992	100. m/0.25 mm/0.5 μm, He, 1. K/min; T_start: 30. C; T_end: 220. C
Packed	SE-30	785.	Buchman, Cao, et al., 1984	He, 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
Packed	SE-30	785.	Peng, Ding, et al., 1988	Supelcoport; 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
Packed	Carbowax 20M	1089.	Buchman, Cao, et al., 1984	He, 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
Capillary	Petrocol DH	776.	Supelco, 2012	100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
Capillary	OV-101	787.	Zenkevich, 2005	25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; T_start: 50. C; T_end: 250. C
Capillary	OV-1	758.	Orav, Kailas, et al., 1999	2. K/min; T_start: 50. C; T_end: 160. C
Capillary	HP-5	765.	Larsen and Frisvad, 1995	35. C @ 2. min, 6. K/min; T_end: 200. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Squalane	784.	Chen, 2008	Program: not specified
Capillary	OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.	784.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
Capillary	OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.	785.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
Packed	SE-30	800.	Robinson and Odell, 1971	N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)
Packed	Squalane	772.	Robinson and Odell, 1971	N2, Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min => 35 => 4C/min => 95C(hold)
Packed	SE-30	800.	Robinson and Odell, 1971, 2	Chrom W; Column length: 6.1 m; Program: 50C(10min) => 20C/min(2min) => 90C(6min) => 10C/min(6min) => (hold at 150C)
Packed	Squalane	772.	Robinson and Odell, 1971, 2	Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min(5min) => 4C/min(15min) => (hold at 95C)

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax FSC	1056.	Tabanca, Kirimer, et al., 2001	60. m/0.25 mm/0.25 μm; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	DB-Wax	1089.	Peng, Yang, et al., 1991	Program: not specified
Capillary	Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.	1089.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	108.9	Donnelly, Abdel-Hamid, et al., 1993	30. 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 thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes

Roth, Bohm, et al., 1983
Roth, W.R.; Bohm, M.; Lenhartz, H-W.; Vogel, E., Heats of hydrogenation. Part 5. Resonance energy of bridged [10]annulenes, Angew. Chem., 1983, 95, 1011-1012. [all data]

Finke H.L., 1956
Finke H.L., 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]

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Evans M.V., 1960
Evans M.V., Vibrational spectra and structure of the tropilidene molecule, J. Am. Chem. Soc., 1960, 82, 1876-1882. [all data]

Roth, Klaerner, et al., 1983
Roth, W.R.; Klaerner, F.G.; Gerit, F.; Grimme, W.; Koeser, H.G.; Busch, R.; Muskulus, B.; Breuckmann, R.; Scholz, B.P.; Lennartz, H.W., Stereochemistry of the bicyclo[2.1.0]pentane ring opening: thermolysis of tricyclo[3.2.0.0(,)]heptane derivatives, Chem. Ber., 1983, 116, 2717-2737. [all data]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E., Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene, J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Gorlitz and Gunther, 1969
Gorlitz, M.; Gunther, H., Protonenresonanz-spektroskopie ungesattigter ringsysteme-XIII, Tetrahedron, 1969, 25, 4467-4480. [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]

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]

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, 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
Tabanca, N.; Kirimer, N.; Can Baser, K.H., The composition of essential oils from two varieties of Sideritis erythrantha var. erythrantha and var. cedretorum, Turk. J. Chem., 2001, 25, 201-208. [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 thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References

Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
S°_gas	Entropy of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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