Adamantane
- Formula: C10H16
- Molecular weight: 136.2340
- 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
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 |
---|---|---|---|---|---|
ΔfH°gas | -134.4 ± 2.3 | kJ/mol | Ccb | Clark, Knox, et al., 1979 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -132.9 ± 1.3 kJ/mol; Gas flow technique for Hs, see Clark, Knox, et al., 1975; ALS |
ΔfH°gas | -138.7 | kJ/mol | N/A | Baroody and Carpenter, 1972 | Value computed using ΔfHsolid° value of -193.8 kj/mol from Baroody and Carpenter, 1972 and ΔsubH° value of 55.1 kj/mol from Clark, Knox, et al., 1979.; DRB |
ΔfH°gas | -133.6 ± 2.5 | kJ/mol | Ccb | Boyd, Sanwal, et al., 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -128.2 ± 4.1 kJ/mol; ALS |
ΔfH°gas | -129. ± 4. | kJ/mol | Ccb | Butler, Carson, et al., 1971 | ALS |
ΔfH°gas | -137.9 ± 0.79 | kJ/mol | Ccr | Mansson, Rapport, et al., 1970 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
87.78 | 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 |
148.91 | 298.15 | ||
150.12 | 300. | ||
215.22 | 400. | ||
274.22 | 500. | ||
323.51 | 600. | ||
398.99 | 800. | ||
452.58 | 1000. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 |
---|---|---|---|---|---|
ΔfH°solid | -192.5 ± 0.4 | kJ/mol | Ccb | Clark, Knox, et al., 1979 | Gas flow technique for Hs, see Clark, Knox, et al., 1975; ALS |
ΔfH°solid | -193.8 | kJ/mol | Ccb | Baroody and Carpenter, 1972 | ALS |
ΔfH°solid | -188.7 ± 2.8 | kJ/mol | Ccb | Boyd, Sanwal, et al., 1971 | ALS |
ΔfH°solid | -188.4 ± 3.3 | kJ/mol | Ccb | Butler, Carson, et al., 1971 | ALS |
ΔfH°solid | -197.2 ± 0.79 | kJ/mol | Ccr | Mansson, Rapport, et al., 1970 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6029. ± 4. | kJ/mol | Ccb | Clark, Knox, et al., 1979 | Gas flow technique for Hs, see Clark, Knox, et al., 1975; Corresponding ΔfHºsolid = -192.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6033.1 ± 2.8 | kJ/mol | Ccb | Boyd, Sanwal, et al., 1971 | Corresponding ΔfHºsolid = -188.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6033.4 ± 3.3 | kJ/mol | Ccb | Butler, Carson, et al., 1971 | Corresponding ΔfHºsolid = -188.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6024.50 ± 0.71 | kJ/mol | Ccr | Mansson, Rapport, et al., 1970 | Corresponding ΔfHºsolid = -197.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 195.83 | J/mol*K | N/A | Westrum, 1961 | crystaline, I phase; DH |
S°solid,1 bar | 195.83 | J/mol*K | N/A | Chang and Westrum, 1960 | crystaline, I phase; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
189.74 | 298.15 | Westrum, 1961 | crystaline, I phase; T = 5 to 350 K. Only values at 298.15 K given.; DH |
189.74 | 298.15 | Chang and Westrum, 1960 | crystaline, I phase; T = 5 to 350 K.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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