Adamantane

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
Δfgas-32.12 ± 0.56kcal/molCcbClark, Knox, et al., 1979Reanalyzed 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
Δfgas-33.15kcal/molN/ABaroody and Carpenter, 1972Value 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
Δfgas-31.93 ± 0.60kcal/molCcbBoyd, Sanwal, et al., 1971Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -30.65 ± 0.98 kcal/mol; ALS
Δfgas-30.8 ± 0.9kcal/molCcbButler, Carson, et al., 1971ALS
Δfgas-32.96 ± 0.19kcal/molCcrMansson, Rapport, et al., 1970ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
20.98200.Boyd R.H., 1971Selected 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
35.590298.15
35.880300.
51.439400.
65.540500.
77.321600.
95.361800.
108.171000.

Condensed phase thermochemistry data

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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
Δfsolid-46.02 ± 0.09kcal/molCcbClark, Knox, et al., 1979Gas flow technique for Hs, see Clark, Knox, et al., 1975; ALS
Δfsolid-46.32kcal/molCcbBaroody and Carpenter, 1972ALS
Δfsolid-45.10 ± 0.68kcal/molCcbBoyd, Sanwal, et al., 1971ALS
Δfsolid-45.02 ± 0.79kcal/molCcbButler, Carson, et al., 1971ALS
Δfsolid-47.14 ± 0.19kcal/molCcrMansson, Rapport, et al., 1970ALS
Quantity Value Units Method Reference Comment
Δcsolid-1441.0 ± 0.9kcal/molCcbClark, Knox, et al., 1979Gas flow technique for Hs, see Clark, Knox, et al., 1975; Corresponding Δfsolid = -46.02 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1441.95 ± 0.68kcal/molCcbBoyd, Sanwal, et al., 1971Corresponding Δfsolid = -45.08 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1442.01 ± 0.78kcal/molCcbButler, Carson, et al., 1971Corresponding Δfsolid = -45.02 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1439.89 ± 0.17kcal/molCcrMansson, Rapport, et al., 1970Corresponding Δfsolid = -47.14 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar46.804cal/mol*KN/AWestrum, 1961crystaline, I phase; DH
solid,1 bar46.804cal/mol*KN/AChang and Westrum, 1960crystaline, I phase; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
45.349298.15Westrum, 1961crystaline, I phase; T = 5 to 350 K. Only values at 298.15 K given.; DH
45.349298.15Chang and Westrum, 1960crystaline, I phase; T = 5 to 350 K.; DH

Phase change data

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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:
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
Tfus552.KN/AAndrews, Carpenter, et al., 1978Crystal phase 1 phase; Uncertainty assigned by TRC = 3. K; TRC
Tfus542.15KN/AMair, Shamaiengar, et al., 1959Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Δvap11.5kcal/molGCvan Roon, Parsons, et al., 2002AC
Δvap12.4kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 403. - 453. K.; AC
Quantity Value Units Method Reference Comment
Δsub14. ± 1.kcal/molAVGN/AAverage of 18 values; Individual data points

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
13.9308.N/AKabo, Blokhin, et al., 2000AC
14.3293.AStephenson and Malanowski, 1987Based on data from 278. - 368. K.; AC
13.2343.AStephenson and Malanowski, 1987Based on data from 328. - 373. K.; AC
13.0358.AStephenson and Malanowski, 1987Based on data from 343. - 483. K. See also Florian, 1968.; AC
14.3 ± 0.2326.TSGCClark, Knox, et al., 1975, 2Based on data from 310. - 336. K.; AC
14.2300.N/ALee and Slutsky, 1975Based on data from 278. - 443. K.; AC
14.2 ± 0.05326.BGBoyd, Sanwal, et al., 1971Based on data from 310. - 336. K.; AC
12.8332.IN/ABased on data from 312. - 366. K.; AC
14.0 ± 0.1333.DBMBratton, Szilard, et al., 1967Based on data from 313. - 353. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
3.30543.2N/AKabo, Blokhin, et al., 2000AC
2.61541.DSCChickos, Hesse, et al., 1998AC
2.61541.2N/ADomalski and Hearing, 1996See also Pirsch, 1966 and Hakvoort, 1993.; AC

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.8069208.62crystaline, IIcrystaline, IWestrum, 1961DH
0.8069208.62crystaline, IIcrystaline, IChang and Westrum, 1960DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
38.67208.62crystaline, IIcrystaline, IWestrum, 1961DH
3.867208.62crystaline, IIcrystaline, IChang and Westrum, 1960DH

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 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 ± 0.04eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.20PEBewick, Edwards, et al., 1976LLK
9.25PIFedorova, Potapov, et al., 1974LLK
9.23PEWorley, Mateescu, et al., 1973LLK
9.1 ± 0.05PESchmidt, Wilkins, et al., 1973LLK
9.3 ± 0.1PEMiller, Koch, et al., 1973LLK
9.31 ± 0.01PERaymonda, 1972LLK
9.30 ± 0.01SRaymonda, 1972LLK
9.22PEMateescu and Workey, 1972LLK
9.25PEDewar and Worley, 1969RDSH
9.75PEJorgensen and Snyder, 1980Vertical value; LLK
9.28PEKovac and Klasinc, 1978Vertical value; LLK
9.75 ± 0.02PEWorrell, Verhoeven, et al., 1974Vertical value; LLK
9.75PESchmidt, 1973Vertical value; LLK
9.55PEBoschi, Schmidt, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H7+10.69?PIFedorova, Potapov, et al., 1974LLK
C7H9+10.69?PIFedorova, Potapov, et al., 1974LLK
C10H15+10.6HPIFedorova, Potapov, et al., 1974LLK

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 113399

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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]

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, IR Spectrum, Mass spectrum (electron ionization), References