Cyclohexane, methylene-

Formula: C₇H₁₂
Molecular weight: 96.1702
IUPAC Standard InChI: InChI=1S/C7H12/c1-7-5-3-2-4-6-7/h1-6H2
IUPAC Standard InChIKey: YULMNMJFAZWLLN-UHFFFAOYSA-N
CAS Registry Number: 1192-37-6
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: Methylenecyclohexane; 1-Methylenecyclohexane
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Gas phase ion energetics data

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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)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.8	PE	Lambert, Xue, et al., 1986	LBLHLM
8.93 ± 0.01	PE	Sarneel, Worrell, et al., 1980	LLK
9.7	EI	Shikhmamedbekova, Aslanov, et al., 1970	RDSH
8.94	PE	Demeo and Yencha, 1970	RDSH
8.97 ± 0.01	PI	Demeo and El-Sayed, 1970	RDSH
9.04 ± 0.03	EI	Winters and Collins, 1968	RDSH
9.13	PE	Spanka and Rademacher, 1986	Vertical value; LBLHLM
9.18	PE	Lambert, Xue, et al., 1986	Vertical value; LBLHLM
9.08 ± 0.01	PE	Sarneel, Worrell, et al., 1980	Vertical value; LLK
9.12 ± 0.02	PE	Martin, Heller, et al., 1974	Vertical value; LLK
9.13	PE	Asmus and Klessinger, 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₃⁺	13.90 ± 0.13	?	EI	Winters and Collins, 1968	RDSH
C₃H₅⁺	13.25 ± 0.11	?	EI	Winters and Collins, 1968	RDSH
C₄H₅⁺	13.10 ± 0.10	?	EI	Winters and Collins, 1968	RDSH
C₄H₆⁺	13.2	C₃H₆	EI	Shikhmamedbekova, Aslanov, et al., 1970	RDSH
C₄H₆⁺	10.94 ± 0.05	?	EI	Winters and Collins, 1968	RDSH
C₄H₇⁺	13.7	C₃H₅	EI	Shikhmamedbekova, Aslanov, et al., 1970	RDSH
C₄H₇⁺	11.34 ± 0.04	?	EI	Winters and Collins, 1968	RDSH
C₅H₇⁺	12.5	C₂H₅	EI	Shikhmamedbekova, Aslanov, et al., 1970	RDSH
C₅H₇⁺	10.45 ± 0.11	C₂H₅	EI	Winters and Collins, 1968	RDSH
C₅H₈⁺	12.2	C₂H₄	EI	Shikhmamedbekova, Aslanov, et al., 1970	RDSH
C₅H₈⁺	10.46 ± 0.08	C₂H₄	EI	Winters and Collins, 1968	RDSH
C₆H₈⁺	11.2	CH₄	EI	Shikhmamedbekova, Aslanov, et al., 1970	RDSH
C₆H₉⁺	10.27 ± 0.08	CH₃	EI	Winters and Collins, 1968	RDSH
C₆H₁₀⁺	11.7	CH₂	EI	Shikhmamedbekova, Aslanov, et al., 1970	RDSH

References

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Lambert, Xue, et al., 1986
Lambert, J.B.; Xue, L.; Bosch, R.J.; Taba, K.M.; Marko, D.E.; Urano, S.; LeBreton, P.R., Through space interactions of double bonds by photoelectron spectroscopy, J. Am. Chem. Soc., 1986, 108, 7575. [all data]

Sarneel, Worrell, et al., 1980
Sarneel, R.; Worrell, C.W.; Pasman, P.; Verhoeven, J.W.; Mes, G.F., The photoelectron spectra of 4-methylene thiacyclohexane derivatives through-bond interaction, Tetrahedron, 1980, 36, 3241. [all data]

Shikhmamedbekova, Aslanov, et al., 1970
Shikhmamedbekova, A.Z.; Aslanov, F.A.; Gadzhiev, M.M.; Gulamova, T.E.; Akhmedova, F.N., Mass spectrometric study of methylene cycloalkenes, Dokl. Phys. Chem., 1970, 26, 34. [all data]

Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J., Photoelectron spectra of bicyclic and exocyclic olefins, J. Chem. Phys., 1970, 53, 4536. [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]

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]

Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P., Transannular interactions in difunctional medium rings. 1. n/π Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy, J. Org. Chem., 1986, 51, 592. [all data]

Martin, Heller, et al., 1974
Martin, H.-D.; Heller, C.; Werp, J., Bishomofulvenkonjugation. Photoelektronenspektren und elektronenstruktur homologer quadricyclane, Chem. Ber., 1974, 107, 1393. [all data]

Asmus and Klessinger, 1974
Asmus, P.; Klessinger, M., Photoelectron spectra of organic compounds. VI. Exocyclic methylene compounds, Tetrahedron, 1974, 30, 2477. [all data]

Notes

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Symbols used in this document:

AE Appearance energy
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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