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
The 3d structure may be viewed using Java or Javascript.
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

Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_fus	552.	K	N/A	Andrews, Carpenter, et al., 1978	Crystal phase 1 phase; Uncertainty assigned by TRC = 3. K; TRC
T_fus	542.15	K	N/A	Mair, Shamaiengar, et al., 1959	Uncertainty assigned by TRC = 1. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	11.5	kcal/mol	GC	van Roon, Parsons, et al., 2002	AC
Δ_vapH°	12.4	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 403. to 453. K.; AC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	14. ± 1.	kcal/mol	AVG	N/A	Average of 18 values; Individual data points

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
13.9	308.	N/A	Kabo, Blokhin, et al., 2000	AC
14.3	293.	A	Stephenson and Malanowski, 1987	Based on data from 278. to 368. K.; AC
13.2	343.	A	Stephenson and Malanowski, 1987	Based on data from 328. to 373. K.; AC
13.0	358.	A	Stephenson and Malanowski, 1987	Based on data from 343. to 483. K. See also Florian, 1968.; AC
14.3 ± 0.2	326.	TSGC	Clark, Knox, et al., 1975, 2	Based on data from 310. to 336. K.; AC
14.2	300.	N/A	Lee and Slutsky, 1975	Based on data from 278. to 443. K.; AC
14.2 ± 0.05	326.	BG	Boyd, Sanwal, et al., 1971	Based on data from 310. to 336. K.; AC
12.8	332.	I	N/A	Based on data from 312. to 366. K.; AC
14.0 ± 0.1	333.	DBM	Bratton, Szilard, et al., 1967	Based on data from 313. to 353. K.; AC

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Method	Reference	Comment
3.30	543.2	N/A	Kabo, Blokhin, et al., 2000	AC
2.61	541.	DSC	Chickos, Hesse, et al., 1998	AC
2.61	541.2	N/A	Domalski and Hearing, 1996	See also Pirsch, 1966 and Hakvoort, 1993.; AC

Enthalpy of phase transition

ΔH_trs (kcal/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
0.8069	208.62	crystaline, II	crystaline, I	Westrum, 1961	DH
0.8069	208.62	crystaline, II	crystaline, I	Chang and Westrum, 1960	DH

Entropy of phase transition

ΔS_trs (cal/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
38.67	208.62	crystaline, II	crystaline, I	Westrum, 1961	DH
3.867	208.62	crystaline, II	crystaline, I	Chang and Westrum, 1960	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

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

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

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]

Andrews, Carpenter, et al., 1978
Andrews, J.T.S.; Carpenter, R.E.; Martinko, T.M.; Fort, R.C.; Flood, T.A.; Adlington, M.G., Transition and Fusion Thermodynamics of Heteroadamantanes, Mol. Cryst. Liq. Cryst., 1978, 41, 357-61. [all data]

Mair, Shamaiengar, et al., 1959
Mair, B.J.; Shamaiengar, M.; Krouskop, N.C.; Rossini, F.D., Isolation of Adamantane from Petroleum, Analytical Chem., 1959, 32, 2082. [all data]

van Roon, Parsons, et al., 2002
van Roon, André; Parsons, John R.; Govers, Harrie A.J., Gas chromatographic determination of vapour pressure and related thermodynamic properties of monoterpenes and biogenically related compounds, Journal of Chromatography A, 2002, 955, 1, 105-115, https://doi.org/10.1016/S0021-9673(02)00200-5 . [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Kabo, Blokhin, et al., 2000
Kabo, G.J.; Blokhin, A.V.; Charapennikau, M.B.; Kabo, A.G.; Sevruk, V.M., Thermodynamic properties of adamantane and the energy states of molecules in plastic crystals for some cage hydrocarbons, Thermochimica Acta, 2000, 345, 2, 125-133, https://doi.org/10.1016/S0040-6031(99)00393-7 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Florian, 1968
Florian, W., Messung des Dampfdruckes von Adamantan, Zeitschrift für Physikalische Chemie, 1968, 61, 5₆, 319-321, https://doi.org/10.1524/zpch.1968.61.5₆.319 . [all data]

Clark, Knox, et al., 1975, 2
Clark, Timothy; Knox, Trevor; Mackle, Henry; McKervey, M. Anthony; Rooney, John J., Heats of sublimation of some cage hydrocarbons by a temperature scanning technique, J. Chem. Soc., Faraday Trans. 1, 1975, 71, 0, 2107, https://doi.org/10.1039/f19757102107 . [all data]

Lee and Slutsky, 1975
Lee, Wen Yaung; Slutsky, L.J., Heat of vaporization, infrared spectrum, and lattice energy of adamantane, J. Phys. Chem., 1975, 79, 24, 2602-2604, https://doi.org/10.1021/j100591a007 . [all data]

Bratton, Szilard, et al., 1967
Bratton, W. Kevin; Szilard, I.; Cupas, Chris A., Enthalpy of sublimation of adamantane, J. Org. Chem., 1967, 32, 6, 2019-2021, https://doi.org/10.1021/jo01281a083 . [all data]

Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul, Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements, Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Pirsch, 1966
Pirsch, Josef, Das kryoskopische Verhalten von organischen Verbindungen mit Adamantan-Struktur, Monatshefte f«65533»r Chemie, 1966, 97, 1, 260-270, https://doi.org/10.1007/BF00905513 . [all data]

Hakvoort, 1993
Hakvoort, G., DSC calibration below 0°C, Calorim. Anal. Therm., 1993, 24, 177. [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

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

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)
T_fus	Fusion (melting) point
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
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
Δ_fusH	Enthalpy of fusion
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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