Adamantane

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Gas 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas-134.4 ± 2.3kJ/molCcbClark, Knox, et al., 1979Reanalyzed 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
Δfgas-138.7kJ/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-133.6 ± 2.5kJ/molCcbBoyd, Sanwal, et al., 1971Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -128.2 ± 4.1 kJ/mol; ALS
Δfgas-129. ± 4.kJ/molCcbButler, Carson, et al., 1971ALS
Δfgas-137.9 ± 0.79kJ/molCcrMansson, Rapport, et al., 1970ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
87.78200.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
148.91298.15
150.12300.
215.22400.
274.22500.
323.51600.
398.99800.
452.581000.

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

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedPMS-1000120.1121.Arutyunov, Kudryashov, et al., 2004N2, Chromaton N-AW-DMCS; Column length: 2. m
PackedSE-30160.1117.Kurbatova, Finkelstein, et al., 2004Chromaton N-AW; Column length: 1. m
PackedSE-30150.1120.L'vova, Kurbatova, et al., 2001N2, N-AW Chromaton; Column length: 1. m
PackedSE-30150.1120.Yashkin, Kurbatova, et al., 2001CHromaton N-AW; Column length: 1. m
PackedC78, Branched paraffin130.1136.9Dallos, Sisak, et al., 2000He; Column length: 3.3 m
PackedPMS-1000160.1149.Kurbatova, Moiseev, et al., 1999N2, Chromatron N-AW; Column length: 1. m
PackedApiezon L160.1116.Kurbatova, Moiseev, et al., 1999N2, Chromatron N-AW; Column length: 1. m
PackedApiezon L200.1116.Kurbatova, Yashkin, et al., 1999N2, Chromaton N-AW; Column length: 1. m
PackedApiezon L200.1116.Kurbatova, Moiseev, et al., 1998Chromaton N-AW; Column length: 1. m
PackedPMS-1000160.1149.Kurbatova, Moiseev, et al., 1998, 2Chromaton N-AW; Column length: 1. m
PackedC78, Branched paraffin130.1135.3Reddy, Dutoit, et al., 1992Chromosorb G HP; Column length: 3.3 m
CapillarySqualane110.1095.2Bender, Said, et al., 1986He; Column length: 100. m; Column diameter: 0.25 mm
CapillarySE-30110.1113.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30120.1117.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30130.1120.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30145.1118.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30150.1116.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane110.1095.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane125.1104.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane140.1114.Bogoslovsky, Anvaer, et al., 1978 
PackedSE-30150.1116.Shlyakhov, Anvaer, et al., 1975 
PackedSE-30120.1117.Mitra, Mohan, et al., 1974N2, Chrom W; Column length: 6.1 m
PackedSE-30130.1120.Mitra, Mohan, et al., 1974N2, Chrom W; Column length: 6.1 m
PackedSE-30140.1125.Mitra, Mohan, et al., 1974N2, Chrom W; Column length: 6.1 m
CapillarySE-30130.1120.Mitra, Mohan, et al., 1974, 2H2; Column length: 6.1 m; Column diameter: 3.18 mm
CapillarySE-30140.1128.Mitra, Mohan, et al., 1974, 2H2; Column length: 6.1 m; Column diameter: 3.18 mm
CapillarySE-30150.1131.Mitra, Mohan, et al., 1974, 2H2; Column length: 6.1 m; Column diameter: 3.18 mm
CapillarySE-30160.1130.Mitra, Mohan, et al., 1974, 2H2; Column length: 6.1 m; Column diameter: 3.18 mm
CapillarySqualane110.1095.Hála, Eyem, et al., 1970N2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySqualane125.1104.Hála, Eyem, et al., 1970N2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySqualane140.1114.Hála, Eyem, et al., 1970N2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySE-30145.1118.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillarySE-30160.1132.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillarySE-30175.1143.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillarySE-30190.1153.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M160.1400.Kurbatova, Finkelstein, et al., 2004Chromaton N-AW; Column length: 1. m
PackedCarbowax 20M150.1325.L'vova, Kurbatova, et al., 2001N2, N-AW Chromaton; Column length: 1. m
PackedCarbowax 20M150.1325.Yashkin, Kurbatova, et al., 2001Column length: 1. m
PackedCarbowax 20M220.1363.Kurbatova, Moiseev, et al., 1998, 3N2, Chromaton N-AW; Column length: 1. m
CapillaryCarbowax 20M145.1320.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillaryCarbowax 20M160.1339.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillaryCarbowax 20M175.1363.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryAdamantyl siloxane160.1123.Konstantinova, Berezkin, et al., 200522. m/0.22 mm/0.20 μm, Nitrogen
CapillaryAdamantyl siloxane160.1123.Konstantinova, Berezkin, et al., 2005, 2Nitrogen; Column length: 22. m; Column diameter: 0.22 mm

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryPetrocol DH1076.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min

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

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane1118.Bayat and Abad, 2011Program: not specified
CapillaryPolydimethyl siloxane1118.Bayat and Abad M.F.Y., 2011Program: not specified
CapillaryApiezon L1144.Finkelstein, Kurbatova, et al., 2002Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1400.Finkelstein, Kurbatova, et al., 2002Program: not specified
CapillaryCarbowax 20M1363.Kurbatova, Kolosova, et al., 2000Program: not specified

References

Go To: Top, Gas phase thermochemistry 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.

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]

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, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References