Bicyclo[3.1.0]hexane

Formula: C₆H₁₀
Molecular weight: 82.1436
IUPAC Standard InChI: InChI=1S/C6H10/c1-2-5-4-6(5)3-1/h5-6H,1-4H2
IUPAC Standard InChIKey: JAPMJSVZDUYFKL-UHFFFAOYSA-N
CAS Registry Number: 285-58-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Stereoisomers:
- cis-Bicyclo[3.1.0]hexane
Other names: Norsabinane; Northujane
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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	39. ± 3.	kJ/mol	Ccb	Chang, McNally, et al., 1970	ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
100.50	298.15	Chang S., 1970	These values were calculated by a method of force field; their uncertainties may exceed 5-10 J/mol*K.; GT
137.99	400.
171.21	500.

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_fH°_liquid	5. ± 3.	kJ/mol	Ccb	Chang, McNally, et al., 1970
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-3795. ± 2.	kJ/mol	Ccb	Chang, McNally, et al., 1970	Corresponding Δ_fHº_liquid = 5.0 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-3818.	kJ/mol	Ccb	Konovalon, 1926	Heat of combustion at 15°C; Corresponding Δ_fHº_liquid = 28. kJ/mol (simple calculation by NIST; no Washburn corrections)

Gas phase ion energetics data

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Data compiled as indicated in comments:
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 C₆H₁₀⁺ (ion structure unspecified)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.28 ± 0.05	EI	Wolkoff and Holmes, 1979	LLK
9.16 ± 0.02	EI	Winters and Collins, 1969	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₃⁺	12.98 ± 0.19	?	EI	Winters and Collins, 1969	RDSH
C₃H₅⁺	11.65 ± 0.14	?	EI	Winters and Collins, 1969	RDSH
C₄H₅⁺	12.62 ± 0.11	?	EI	Winters and Collins, 1969	RDSH
C₄H₆⁺	10.28 ± 0.05	?	EI	Winters and Collins, 1969	RDSH
C₅H₅⁺	13.20 ± 0.12	?	EI	Winters and Collins, 1969	RDSH
C₅H₇⁺	9.88 ± 0.05	CH₃	EI	Wolkoff and Holmes, 1979	LLK
C₅H₇⁺	9.68 ± 0.07	CH₃	EI	Winters and Collins, 1969	RDSH
C₆H₇⁺	11.60 ± 0.15	H₂+H	EI	Winters and Collins, 1969	RDSH
C₆H₉⁺	10.20 ± 0.10	H	EI	Winters and Collins, 1969	RDSH

References

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

Chang, McNally, et al., 1970
Chang, Sho-ju.; McNally, D.; Shary-Tehrany, S.; Hickey, S.M.J.; Boyd, R.H., The heats of combustion and strain energies of bicylo[n.m.O]alkanes, J. Am. Chem. Soc., 1970, 92, 3109-3118. [all data]

Chang S., 1970
Chang S., The heats of combustion and strain energies of bicyclo[n.m.0]alkanes, J. Am. Chem. Soc., 1970, 92, 3109-3118. [all data]

Konovalon, 1926
Konovalon, D.-P., Sur Les Chaleurs de Combustion de Quelques hydrocarbures cycliques, J. Chim. Phys., 1926, 23, 359-362. [all data]

Wolkoff and Holmes, 1979
Wolkoff, P.; Holmes, J.L., Isomeric cyclic [C₆H₁₀]⁺ ions. The energy barrier to ring opening, Can. J. Chem., 1979, 57, 348. [all data]

Winters and Collins, 1969
Winters, R.E.; Collins, J.H., Mass spectrometric studies of structural isomers. II.Mono- and bicyclic C₆H₁₀ molecules, Org. Mass Spectrom., 1969, 2, 299. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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