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1-Methyladamantane

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-171.7 ± 2.6kJ/molCcbClark, Knox, et al., 1979Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -169.7 ± 1.4 kJ/mol; Gas flow technique for Hs,see Clark, Knox, et al., 1975
Deltafgas-171.5 ± 2.9kJ/molCcbSteele and Watt, 1977Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -175. ± 2. kJ/mol

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafsolid-237.3 ± 1.3kJ/molCcbClark, Knox, et al., 1979Gas flow technique for Hs,see Clark, Knox, et al., 1975
Deltafsolid-243. ± 2.kJ/molCcbSteele and Watt, 1977 
Quantity Value Units Method Reference Comment
Deltacsolid-6663.8 ± 1.3kJ/molCcbClark, Knox, et al., 1979Gas flow technique for Hs,see Clark, Knox, et al., 1975; Corresponding «DELTA»fsolid = -237.3 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-6658. ± 2.kJ/molCcbSteele and Watt, 1977Corresponding «DELTA»fsolid = -243. kJ/mol (simple calculation by NIST; no Washburn corrections)

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, Kenneth Kroenlein director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tfus392.KN/AClark, Knox, et al., 1977Crystal phase 1 phase; Uncertainty assigned by TRC = 3.71 K; TRC
Quantity Value Units Method Reference Comment
Deltasub67.57kJ/molVClark, Knox, et al., 1979Gas flow technique for Hs,see Clark, Knox, et al., 1975; ALS
Deltasub65.6kJ/molN/AClark, Knox, et al., 1979DRB
Deltasub68. ± 1.kJ/molVSteele and Watt, 1977ALS
Deltasub71.5kJ/molN/ASteele and Watt, 1977DRB
Deltasub67.8 ± 1.3kJ/molBGSteele and Watt, 1977Based on data from 300. - 342. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Reference Comment
67.6 ± 0.5321.Clark, Knox, et al., 1975, 2Based on data from 306. - 336. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
3.71392.Clark, Knox, et al., 1977AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
11.27169.5Clark, Knox, et al., 1977CAL
6.95211.5
9.46392.

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:


Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

2-Methyladamantane = 1-Methyladamantane

By formula: C11H18 = C11H18

Quantity Value Units Method Reference Comment
Deltar-14.1 ± 0.46kJ/molEqkEngler, Blanchard, et al., 1972liquid phase; GLC

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 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

IE (eV) Method Reference Comment
9.17 ± 0.02PEWorley, Mateescu, et al., 1973LLK
9.24PEBodor, Dewar, et al., 1970RDSH

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
CapillarySE-30190.1171.Sarkisova and Pimerzin, 2005He; Column length: 50. m; Column diameter: 0.2 mm
PackedSE-30150.1140.Yashkin, Kurbatova, et al., 2001CHromaton N-AW; Column length: 1. m
CapillarySqualane110.1115.3Bender, Said, et al., 1986He; Column length: 100. m; Column diameter: 0.25 mm
CapillarySE-30110.1118.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30120.1124.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30130.1128.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30140.1134.Bogoslovsky, Anvaer, et al., 1978 
CapillarySE-30145.1137.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane100.1110.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane110.1116.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane125.1125.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane140.1135.Bogoslovsky, Anvaer, et al., 1978 
PackedSE-30120.1124.Mitra, Mohan, et al., 1974N2, Chrom W; Column length: 6.1 m
PackedSE-30130.1128.Mitra, Mohan, et al., 1974N2, Chrom W; Column length: 6.1 m
PackedSE-30140.1134.Mitra, Mohan, et al., 1974N2, Chrom W; Column length: 6.1 m
CapillarySqualane100.1110.Mitra, Mohan, et al., 1974, 2H2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySqualane100.1162.Mitra, Mohan, et al., 1974, 2H2; Column length: 50. m; Column diameter: 0.2 mm
CapillaryApiezon L140.1179.Hála, Eyem, et al., 1970N2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySqualane110.1116.Hála, Eyem, et al., 1970N2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySqualane125.1125.Hála, Eyem, et al., 1970N2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySqualane140.1135.Hála, Eyem, et al., 1970N2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySE-30145.1137.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillarySE-30160.1151.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillarySE-30175.1162.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillarySE-30190.1171.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm

Kovats' RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryHP-5MS1100.Yang, Wang, et al., 200630. m/0.25 mm/0.25 «mu»m, 50. C @ 2. min, 6. K/min; Tend: 300. C

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M150.1315.Yashkin, Kurbatova, et al., 2001Column length: 1. m
CapillaryCarbowax 20M145.1313.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillaryCarbowax 20M160.1325.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm
CapillaryCarbowax 20M175.1348.Burkhard, Vais, et al., 1969N2; Column length: 50. m; Column diameter: 0.27 mm

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

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane1137.Bayat and Abad, 2011Program: not specified
CapillaryPolydimethyl siloxane1137.Bayat and Abad M.F.Y., 2011Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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]

Steele and Watt, 1977
Steele, W.V.; Watt, I., The standard enthalpies of formation of adamantanoid compounds 4. Methyladamantanes, J. Chem. Thermodyn., 1977, 9, 843-849. [all data]

Clark, Knox, et al., 1977
Clark, Timothy; Knox, Trevor Mc.O.; Mackle, Henry; McKervey, M. Anthony, Order--disorder transitions in substituted adamantanes, J. Chem. Soc., Faraday Trans. 1, 1977, 73, 0, 1224, https://doi.org/10.1039/f19777301224 . [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]

Engler, Blanchard, et al., 1972
Engler, E.M.; Blanchard, K.R.; Schleyer, P.v.R., Enhanced axial-equatorial enthalpy differences in the methyl adamantanes, J. Chem. Soc. Chem. Commun., 1972, 1210-1212. [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]

Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method, J. Am. Chem. Soc., 1970, 92, 19. [all data]

Sarkisova and Pimerzin, 2005
Sarkisova, V.S.; Pimerzin, A.A., Gas chromatographic characteristics and boiling points of diadamantanes, Pet. Chem. USSR (Engl. Transl.), 2005, 45, 1, 63-66. [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]

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]

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]

Yang, Wang, et al., 2006
Yang, C.; Wang, Z.D.; Hollebone, B.P.; Peng, X.; Fingas, M.; Landriault, M., GC/MS Quantitation of diamondoid compounds in crude oils and petroleum products, Environmental Forensics, 2006, 7, 4, 377-390, https://doi.org/10.1080/15275920600996396 . [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]


Notes

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