1,3,5,7-Tetramethyl-adamantane

• Formula: C₁₄H₂₄
• Molecular weight: 192.3404
• IUPAC Standard InChI:
  

  InChI=1S/C14H24/c1-11-5-12(2)8-13(3,6-11)10-14(4,7-11)9-12/h5-10H2,1-4H3 Download the identifier in a file.

• IUPAC Standard InChIKey: UJSORZVCMMYGBS-UHFFFAOYSA-N
• CAS Registry Number: 1687-36-1
• Chemical structure:
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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
fH°gas	-284.6 ± 6.9	kJ/mol	Ccb	Clark, Knox, et al., 1979	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -281.0 ± 2.1 kJ/mol; Gas flow technique for Hs, see Clark, Knox, et al., 1975
fH°gas	-282.1 ± 7.0	kJ/mol	Ccb	Steele and Watt, 1977	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -295. ± 4. 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
fH°solid	-362.1 ± 1.9	kJ/mol	Ccb	Clark, Knox, et al., 1979	Gas flow technique for Hs, see Clark, Knox, et al., 1975
fH°solid	-379. ± 4.	kJ/mol	Ccb	Steele and Watt, 1977
Quantity	Value	Units	Method	Reference	Comment
cH°solid	-8577.0 ± 2.0	kJ/mol	Ccb	Clark, Knox, et al., 1979	Gas flow technique for Hs, see Clark, Knox, et al., 1975; Corresponding «DELTA»fHºsolid = -362.1 kJ/mol (simple calculation by NIST; no Washburn corrections)
cH°solid	-8560. ± 4.	kJ/mol	Ccb	Steele and Watt, 1977	Corresponding «DELTA»fHºsolid = -379. 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
Tfus	337.2	K	N/A	Clark, Knox, et al., 1977	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity	Value	Units	Method	Reference	Comment
subH°	81.13	kJ/mol	V	Clark, Knox, et al., 1979	Gas flow technique for Hs, see Clark, Knox, et al., 1975; ALS
subH°	77.5	kJ/mol	N/A	Clark, Knox, et al., 1979	DRB
subH°	84. ± 1.	kJ/mol	V	Steele and Watt, 1977	ALS
subH°	96.9	kJ/mol	N/A	Steele and Watt, 1977	DRB
subH°	83.7 ± 1.3	kJ/mol	BG	Steele and Watt, 1977	Based on data from 310. - 350. K.; AC

Enthalpy of sublimation

subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
81. ± 11.	305.	TSGC	Clark, Knox, et al., 1975, 2	Based on data from 295. - 315. K.; AC

Enthalpy of fusion

fusH (kJ/mol)	Temperature (K)	Reference	Comment
9.82	337.2	Clark, Knox, et al., 1977	AC

Entropy of fusion

fusS (J/mol*K)	Temperature (K)	Reference	Comment
1.25	183.3	Clark, Knox, et al., 1977	CAL
29.12	337.2

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 by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

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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Kovats' RI, non-polar column, temperature ramp

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References

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

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]

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]

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]

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]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  cH°solid	Enthalpy of combustion of solid at standard conditions
  fH°gas	Enthalpy of formation of gas at standard conditions
  fH°solid	Enthalpy of formation of solid at standard conditions
  fusH	Enthalpy of fusion
  fusS	Entropy of fusion
  subH	Enthalpy of sublimation
  subH°	Enthalpy of sublimation at standard conditions

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