Adamantane

Formula: C₁₀H₁₆
Molecular weight: 136.2340
IUPAC Standard InChI: InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2
IUPAC Standard InChIKey: ORILYTVJVMAKLC-UHFFFAOYSA-N
CAS Registry Number: 281-23-2
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: Tricyclo[3.3.1.1(3,7)]decane; Tricyclo(3,3,1,1,^3,7)-decane; tricyclo[3.3.1.13,7]decane
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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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-32.12 ± 0.56	kcal/mol	Ccb	Clark, Knox, et al., 1979	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -31.76 ± 0.32 kcal/mol; Gas flow technique for Hs, see Clark, Knox, et al., 1975; ALS
Δ_fH°_gas	-33.15	kcal/mol	N/A	Baroody and Carpenter, 1972	Value computed using Δ_fH_solid° value of -193.8 kj/mol from Baroody and Carpenter, 1972 and Δ_subH° value of 55.1 kj/mol from Clark, Knox, et al., 1979.; DRB
Δ_fH°_gas	-31.93 ± 0.60	kcal/mol	Ccb	Boyd, Sanwal, et al., 1971	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -30.65 ± 0.98 kcal/mol; ALS
Δ_fH°_gas	-30.8 ± 0.9	kcal/mol	Ccb	Butler, Carson, et al., 1971	ALS
Δ_fH°_gas	-32.96 ± 0.19	kcal/mol	Ccr	Mansson, Rapport, et al., 1970	ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
20.98	200.	Boyd R.H., 1971	Selected values were obtained by force field calculation. One can expect the uncertainty in Cp(T) values to be about 10 J/mol*K if compare with the authors' results for bicyclo[2.2.1]heptane.; GT
35.590	298.15
35.880	300.
51.439	400.
65.540	500.
77.321	600.
95.361	800.
108.17	1000.

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-46.02 ± 0.09	kcal/mol	Ccb	Clark, Knox, et al., 1979	Gas flow technique for Hs, see Clark, Knox, et al., 1975; ALS
Δ_fH°_solid	-46.32	kcal/mol	Ccb	Baroody and Carpenter, 1972	ALS
Δ_fH°_solid	-45.10 ± 0.68	kcal/mol	Ccb	Boyd, Sanwal, et al., 1971	ALS
Δ_fH°_solid	-45.02 ± 0.79	kcal/mol	Ccb	Butler, Carson, et al., 1971	ALS
Δ_fH°_solid	-47.14 ± 0.19	kcal/mol	Ccr	Mansson, Rapport, et al., 1970	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-1441.0 ± 0.9	kcal/mol	Ccb	Clark, Knox, et al., 1979	Gas flow technique for Hs, see Clark, Knox, et al., 1975; Corresponding Δ_fHº_solid = -46.02 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1441.95 ± 0.68	kcal/mol	Ccb	Boyd, Sanwal, et al., 1971	Corresponding Δ_fHº_solid = -45.08 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1442.01 ± 0.78	kcal/mol	Ccb	Butler, Carson, et al., 1971	Corresponding Δ_fHº_solid = -45.02 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1439.89 ± 0.17	kcal/mol	Ccr	Mansson, Rapport, et al., 1970	Corresponding Δ_fHº_solid = -47.14 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	46.804	cal/mol*K	N/A	Westrum, 1961	crystaline, I phase; DH
S°_{solid,1 bar}	46.804	cal/mol*K	N/A	Chang and Westrum, 1960	crystaline, I phase; DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
45.349	298.15	Westrum, 1961	crystaline, I phase; T = 5 to 350 K. Only values at 298.15 K given.; DH
45.349	298.15	Chang and Westrum, 1960	crystaline, I phase; T = 5 to 350 K.; DH

Gas phase ion energetics data

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Data evaluated as indicated in comments:
L - Sharon G. Lias

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

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.25 ± 0.04	eV	N/A	N/A	L

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.20	PE	Bewick, Edwards, et al., 1976	LLK
9.25	PI	Fedorova, Potapov, et al., 1974	LLK
9.23	PE	Worley, Mateescu, et al., 1973	LLK
9.1 ± 0.05	PE	Schmidt, Wilkins, et al., 1973	LLK
9.3 ± 0.1	PE	Miller, Koch, et al., 1973	LLK
9.31 ± 0.01	PE	Raymonda, 1972	LLK
9.30 ± 0.01	S	Raymonda, 1972	LLK
9.22	PE	Mateescu and Workey, 1972	LLK
9.25	PE	Dewar and Worley, 1969	RDSH
9.75	PE	Jorgensen and Snyder, 1980	Vertical value; LLK
9.28	PE	Kovac and Klasinc, 1978	Vertical value; LLK
9.75 ± 0.02	PE	Worrell, Verhoeven, et al., 1974	Vertical value; LLK
9.75	PE	Schmidt, 1973	Vertical value; LLK
9.55	PE	Boschi, Schmidt, et al., 1973	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₇⁺	10.69	?	PI	Fedorova, Potapov, et al., 1974	LLK
C₇H₉⁺	10.69	?	PI	Fedorova, Potapov, et al., 1974	LLK
C₁₀H₁₅⁺	10.6	H	PI	Fedorova, Potapov, et al., 1974	LLK

References

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Clark, Knox, et al., 1979
Clark, T.; Knox, T.M.O.; McKervey, M.A.; Mackle, H.; Rooney, J.J., Thermochemistry of bridged-ring substances. Enthalpies of formation of some diamondoid hydrocarbons and of perhydroquinacene. Comparisons with data from empirical force field calculations, J. Am. Chem. Soc., 1979, 101, 2404-2410. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Clark, Knox, et al., 1975
Clark, T.; Knox, T.M.; Mackle, H.; McKervey, M.A.; Rooney, J.J., Calorimetric evaluation of enthalpies of formation of some bridged-ring hydrocarbons. Comparison with data from empirical force field calculations., J. Am. Chem. Soc., 1975, 97, 3835-3836. [all data]

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

Boyd, Sanwal, et al., 1971
Boyd, R.H.; Sanwal, S.N.; Shary-Tehrany, S.; McNally, D., The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons, J. Phys. Chem., 1971, 75, 1264-1271. [all data]

Butler, Carson, et al., 1971
Butler, R.S.; Carson, A.S.; Laye, P.G.; Steele, W.V., The enthalpy of formation of adamantane, J. Chem. Thermodyn., 1971, 3, 277-280. [all data]

Mansson, Rapport, et al., 1970
Mansson, M.; Rapport, N.; Westrum, E.F., Jr., Enthalpies of formation of globular molecules. I. Adamantane and hexamethylenetetramine, J. Am. Chem. Soc., 1970, 92, 7296-7299. [all data]

Boyd R.H., 1971
Boyd R.H., The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons, J. Phys. Chem., 1971, 75, 1264-1271. [all data]

Westrum, 1961
Westrum, E.F., Jr., The thermophysical properties of three globular molecules, J. Phys. Chem. Solids, 1961, 18, 83-85. [all data]

Chang and Westrum, 1960
Chang, S.-S.; Westrum, E.F., Jr., Heat capacities and thermodynamic properties of globular molecules. I. Adamantane and hexamethylenetetramine, J. Phys. Chem., 1960, 64, 1547-1551. [all data]

Bewick, Edwards, et al., 1976
Bewick, A.; Edwards, C.J.; Jones, S.R.; Mellor, J.M., The electrochemical difunctionalisation of saturated hydrocarbons, Tetrahedron Lett., 1976, 631. [all data]

Fedorova, Potapov, et al., 1974
Fedorova, M.S.; Potapov, V.K.; Denisov, Yu.V.; Sorokin, V.V.; Evlasheva, T.I., A mass-spectrometric study of the photoionisation of certain cyclic hydrocarbons, Russ. J. Phys. Chem., 1974, 48, 1078, In original 1828. [all data]

Worley, Mateescu, et al., 1973
Worley, S.D.; Mateescu, G.D.; McFarland, C.W.; Fort, R.C., Jr.; Sheley, C.F., Photoelectron spectra and MINDO-SCF-MO calculations for adamantane and some of its derivatives, J. Am. Chem. Soc., 1973, 95, 7580. [all data]

Schmidt, Wilkins, et al., 1973
Schmidt, W.; Wilkins, B.T.; Fritz, G.; Huber, R., Energy level trends in 1,3,5,7-tetrasilaadamantanes ("carborundanes") and related molecules from photoelectron spectroscopy, J. Organomet. Chem., 1973, 59, 109. [all data]

Miller, Koch, et al., 1973
Miller, L.L.; Koch, V.R.; Koenig, T.; Tuttle, M., Photoelectron spectroscopy and the anodic fragmentation of adamantane derivatives, J. Am. Chem. Soc., 1973, 95, 5075. [all data]

Raymonda, 1972
Raymonda, J.W., Rydberg states in cyclic alkanes, J. Chem. Phys., 1972, 56, 3912. [all data]

Mateescu and Workey, 1972
Mateescu, G.D.; Workey, S.D., Electron spectroscipy. II. Photoelectron spectra of adamantane and 1-bromoadamantane,, Tetrahedron Lett., 1972, 52, 5285. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Jorgensen and Snyder, 1980
Jorgensen, F.S.; Snyder, J.P., Search for a trans-disulfide: Structural analysis of di-tert- adamantyl disulfide by photoelectron spectroscopy, derivation of σ(t-Ad), and molecular mechanics calculations for related bulky disulfides, J. Org. Chem., 1980, 45, 1015. [all data]

Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L., Photoelectron spectroscopy of adamantane and some adamantanones, Croat. Chem. Acta, 1978, 51, 55. [all data]

Worrell, Verhoeven, et al., 1974
Worrell, C.; Verhoeven, J.W.; Speckamp, W.N., Through-bond interaction in 1-aza-adamantane derivatives, Tetrahedron, 1974, 30, 3525. [all data]

Schmidt, 1973
Schmidt, W., Photoelectron spectra of diamondoid molecules, adamantane, silamantane and urotropine, Tetrahedron, 1973, 29, 2129. [all data]

Boschi, Schmidt, et al., 1973
Boschi, R.; Schmidt, W.; Suffolk, R.J.; Wilkins, B.T.; Lempka, H.J.; Ridyard, J.N.A., Complete valence shell electronic structure of adamantane from He I and He II photoelectron spectroscopy, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 377. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,solid	Constant pressure heat capacity of solid
IE (evaluated)	Recommended ionization energy
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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