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 Copy

  
• IUPAC Standard InChIKey: ORILYTVJVMAKLC-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Phase change data

Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
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

Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

Go To: Top, Phase change data, Gas Chromatography, 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

Ionization energy determinations

Appearance energy determinations

Gas Chromatography

Go To: Top, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, custom temperature program

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References

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

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

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
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]

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]

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]

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]

Arutyunov, Kudryashov, et al., 2004
Arutyunov, Y.I.; Kudryashov, S.Y.; Onuchak, L.A., Analysis of Mixtures Containing Unknown Components by Gas Chromatography: Determination of Molecular Mass, J. Anal. Chem. USSR (Engl. Transl.), 2004, 59, 4, 358-365. [all data]

Kurbatova, Finkelstein, et al., 2004
Kurbatova, S.V.; Finkelstein, E.E.; Kolosova, E.A.; Kartashev, A.V.; Rashkin, S.V., Structural analogy method in studies of adamantanes, J. Struct. Chem., 2004, 45, 1, 144-150, https://doi.org/10.1023/B:JORY.0000041513.82837.4e . [all data]

L'vova, Kurbatova, et al., 2001
L'vova, N.Yu.; Kurbatova, S.V.; Yashkin, S.N.; Kolosova, E.A., Gas chromatography of halogenated adamantanes, Russ. J. Phys. Chem. (Engl. Transl.), 2001, 75, 12, 2053-2056. [all data]

Yashkin, Kurbatova, et al., 2001
Yashkin, S.N.; Kurbatova, S.V.; Buryak, A.K., Gas chromatography of halogenated adamantanes, Russ. Chem. Bull. (Engl. Transl.), 2001, 50, 5, 828-832, https://doi.org/10.1023/A:1011350908009 . [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Kurbatova, Moiseev, et al., 1999
Kurbatova, S.V.; Moiseev, I.K.; Kudryashov, S.Yu.; Yashkin, S.N.; Postnikova, I.V., Chromatographic examination of the intermediate products of midantane synthesis, J. Anal. Chem. USSR (Engl. Transl.), 1999, 54, 1, 75-77. [all data]

Kurbatova, Yashkin, et al., 1999
Kurbatova, S.V.; Yashkin, S.N.; Moiseev, I.K.; Zemtsova, M.N., A study of the cell effect for adamantane derivatives by gas-liquid chromatography, Russ. J. Phys. Chem. (Engl. Transl.), 1999, 73, 9, 1486-1489. [all data]

Kurbatova, Moiseev, et al., 1998
Kurbatova, S.V.; Moiseev, I.K.; Zemtsova, M.N.; Kudryashov, S.Yu., Gas chromatography of aminoadamantanes, J. Anal. Chem. USSR (Engl. Transl.), 1998, 53, 8, 732-734. [all data]

Kurbatova, Moiseev, et al., 1998, 2
Kurbatova, S.V.; Moiseev, I.K.; Klimochkin, Yu.N.; Arutyunov, Yu.N., Chromatography analysis of intermediates in the synthesis of remantadin, J. Anal. Chem. USSR (Engl. Transl.), 1998, 53, 9, 865-868. [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Bender, Said, et al., 1986
Bender, A.O.; Said, E.Z.; Abdulsada, A.K., Gas chromatographic identification of adamantanes in some Iraqi crude oils, Analyst, 1986, 111, 5, 575-576, https://doi.org/10.1039/an9861100575 . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I., On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices, Zh. Anal. Khim., 1975, 30, 788-792. [all data]

Mitra, Mohan, et al., 1974
Mitra, G.D.; Mohan, G.; Sinha, A., Advances in the utilization of the retention index system for characterizing hydrocarbons in complex mixtures by gas chromatography, J. Chromatogr., 1974, 99, 215-230, https://doi.org/10.1016/S0021-9673(00)90857-4 . [all data]

Mitra, Mohan, et al., 1974, 2
Mitra, G.D.; Mohan, G.; Sinha, A., Gas chromatographic analysis of complex hydrocarbon mixtures, J. Chromatogr. A, 1974, 91, 633-648, https://doi.org/10.1016/S0021-9673(01)97944-0 . [all data]

Hála, Eyem, et al., 1970
Hála, S.; Eyem, J.; Burkhard, J.; Landa, S., Retention indices of adamantanes, J. Chromatogr. Sci., 1970, 8, 4, 203-209, https://doi.org/10.1093/chromsci/8.4.203 . [all data]

Burkhard, Vais, et al., 1969
Burkhard, J.; Vais, J.; Vodicka, L.; Landa, S., Adamantane and its derivatives. XVI. The gas chromatographic characterization of adamantane derivatives, J. Chromatogr., 1969, 42, 207-218, https://doi.org/10.1016/S0021-9673(01)80617-8 . [all data]

Kurbatova, Moiseev, et al., 1998, 3
Kurbatova, S.V.; Moiseev, I.K.; Zemtsova, M.N., Regularities in chromatographic retention of some adamantane derivatives, J. Anal. Chem. USSR (Engl. Transl.), 1998, 53, 1, 41-43. [all data]

Konstantinova, Berezkin, et al., 2005
Konstantinova, K.K.; Berezkin, V.G.; Kurbatova, S.V.; Finkel'shtein, E.E., Relationship between physicochemical properties and chromatographic retention of some adamantane derivatives, Russ. J. Appl. Chem. (Engl. Transl.), 2005, 78, 9, 1498-1502, https://doi.org/10.1007/s11167-005-0546-y . [all data]

Konstantinova, Berezkin, et al., 2005, 2
Konstantinova, K.K.; Berezkin, V.G.; Kurbatova, S.V.; Finkel'stein, E.E., Relationship between Physicochemical Properties and Chromatographic Retention of Some Adamantane Derivatives, Rus. J. Applied Chem., 2005, 78, 9, 1522-1526, https://doi.org/10.1007/s11167-005-0546-y . [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]

Bayat and Abad, 2011
Bayat, Z.; Abad, M.F.Y., Quantitative structure-property relationship (QSPR) study of Kovats retention indices of some of adamantane derivatives by the genetic algorithm amd nultiply linear regression (GA-MLR) method, Petroleum Coal, 2011, 53, 2, 132-140. [all data]

Bayat and Abad M.F.Y., 2011
Bayat, Z.; Abad M.F.Y., Computational approaches to the prediction of the Kovats retention index (RI) for adamantane derivatives (AD) as a drug, J. Chem. Pharm. Res., 2011, 3, 1, 48-55. [all data]

Finkelstein, Kurbatova, et al., 2002
Finkelstein, E.E.; Kurbatova, S.V.; Kolosova, E.A., Study of biological activity of structure analogies of adamantane, Proc. Samara State Univ., 2002, 26, 4, 121-128. [all data]

Kurbatova, Kolosova, et al., 2000
Kurbatova, S.; Kolosova, E.; Solovova, N.; Finkelshtein, E.; Zemtsova, M., Gas-chromatographic investigation of adamantane oxygen derivatives, Vestn. Samara State Univ., 2000, 4, 18, 167-172. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Tfus	Fusion (melting) point
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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