Cyclohexene, 1-methyl-

Formula: C₇H₁₂
Molecular weight: 96.1702
IUPAC Standard InChI: InChI=1S/C7H12/c1-7-5-3-2-4-6-7/h5H,2-4,6H2,1H3
IUPAC Standard InChIKey: CTMHWPIWNRWQEG-UHFFFAOYSA-N
CAS Registry Number: 591-49-1
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: α-Methylcyclohexene; 1-Methylcyclohexene; 1-Methyl-1-cyclohexene; 1-Methylcyclohex-1-ene; 1-Methylcyclohexene-1
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Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1048.85 ± 0.16	kcal/mol	Ccb	Labbauf and Rossini, 1961	Corresponding Δ_fHº_liquid = -19.40 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-1047.3	kcal/mol	Ccb	Zubova, 1901	Corresponding Δ_fHº_liquid = -20.9 kcal/mol (simple calculation by NIST; no Washburn corrections)

Gas phase ion energetics data

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

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₇H₁₂⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	197.2	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	189.4	kcal/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.67 ± 0.02	PE	Rang, Paldoia, et al., 1974	LLK
8.67 ± 0.02	EI	Winters and Collins, 1968	RDSH
8.69 ± 0.05	PE	Baidin, Timoshenko, et al., 1985	Vertical value; LBLHLM

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₃⁺	14.06 ± 0.13	?	EI	Winters and Collins, 1968	RDSH
C₃H₅⁺	13.46 ± 0.09	?	EI	Winters and Collins, 1968	RDSH
C₄H₅⁺	13.22 ± 0.10	?	EI	Winters and Collins, 1968	RDSH
C₄H₆⁺	11.02 ± 0.08	?	EI	Winters and Collins, 1968	RDSH
C₄H₇⁺	11.48 ± 0.05	?	EI	Winters and Collins, 1968	RDSH
C₅H₇⁺	10.47 ± 0.07	C₂H₅	EI	Winters and Collins, 1968	RDSH
C₅H₈⁺	10.56 ± 0.15	C₂H₄	EI	Winters and Collins, 1968	RDSH
C₆H₉⁺	10.27 ± 0.09	CH₃	EI	Winters and Collins, 1968	RDSH
C₇H₁₁⁺	10.78 ± 0.05	H	EI	Blanchette, Holmes, et al., 1987	LBLHLM

References

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

Labbauf and Rossini, 1961
Labbauf, A.; Rossini, F.D., Heats of combustion, formation, and hydrogenation of 14 selected cyclomonoolefin hydrocarbons, J. Phys. Chem., 1961, 65, 476-480. [all data]

Zubova, 1901
Zubova, P., Data about heat of combustion of compound cycle structure, Zh. Fiz. Khim., 1901, 33, 708-722. [all data]

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]

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]

Baidin, Timoshenko, et al., 1985
Baidin, V.N.; Timoshenko, M.M.; Chizhov, Y.V.; Ustynyuk, Y.A.; Kritskaya, I.I., Photoelectron spectra nad the structure of organomercury compounds, J. Organomet. Chem., 1985, 292, 55. [all data]

Blanchette, Holmes, et al., 1987
Blanchette, M.C.; Holmes, J.L.; Lossing, F.P., Characterizing the 2-norbornyl cation in the gas phase, J. Am. Chem. Soc., 1987, 109, 1392. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References

Symbols used in this document:

AE Appearance energy

Δ_cH°_liquid Enthalpy of combustion of liquid at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions