Adamantane, 1,3-dimethyl-
- Formula: C12H20
- Molecular weight: 164.2872
- IUPAC Standard InChIKey: CWNOIUTVJRWADX-UHFFFAOYSA-N
- CAS Registry Number: 702-79-4
- 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, 1,3-dimethyl-; 1,3-Dimethyladamantane; 1,3-dimethyltricyclo[3.3.1.13,7]decane
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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.
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 |
---|---|---|---|---|---|
Tboil | 471. | K | N/A | Anonymous, 1969 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 245.0 | K | N/A | Clark, Knox, et al., 1977 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 708. | K | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 30.00 | bar | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 2.50 bar; from extraploation of obs. vapor pressures to Tc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 1.750 | mol/l | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 0.073 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 49.7 ± 0.2 | kJ/mol | C | Varushchenko, Pashchenko, et al., 2001 | AC |
ΔvapH° | 49.4 ± 0.3 | kJ/mol | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 352. to 526. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 68. ± 1. | kJ/mol | V | Steele and Watt, 1977 | ALS |
ΔsubH° | 68.0 | kJ/mol | N/A | Steele and Watt, 1977 | DRB |
ΔsubH° | 67.8 ± 1.3 | kJ/mol | EB | Steele and Watt, 1977 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
49.2 ± 0.2 | 308. | C | Varushchenko, Pashchenko, et al., 2001 | AC |
45.9 ± 0.3 | 360. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 352. to 526. K.; AC |
43.7 ± 0.3 | 400. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 352. to 526. K.; AC |
41.5 ± 0.3 | 440. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 352. to 526. K.; AC |
39.1 ± 0.3 | 480. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 352. to 526. K.; AC |
36.4 ± 0.3 | 520. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 352. to 526. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
1.54 | 247.8 | AC | Varushchenko, Druzhinina, et al., 2005 | Based on data from 8. to 373. K.; AC |
0.94 | 244. | DSC | Arntz and Schneider, 1980 | AC |
0.92 | 245. | N/A | Clark, Knox, et al., 1977 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.3 | 221. | Clark, Knox, et al., 1977 | CAL |
3.76 | 245. |
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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.15 | PE | Bewick, Edwards, et al., 1976 | LLK |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 190. | 1184. | Sarkisova and Pimerzin, 2005 | He; Column length: 50. m; Column diameter: 0.2 mm |
Packed | PMS-1000 | 120. | 1130. | Arutyunov, Kudryashov, et al., 2004 | N2, Chromaton N-AW-DMCS; Column length: 2. m |
Capillary | Squalane | 110. | 1136. | Bogoslovsky, Anvaer, et al., 1978 | |
Capillary | Squalane | 125. | 1144. | Bogoslovsky, Anvaer, et al., 1978 | |
Capillary | Squalane | 140. | 1154. | Bogoslovsky, Anvaer, et al., 1978 | |
Capillary | Squalane | 100. | 1130. | Mitra, Mohan, et al., 1974 | H2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | Apiezon L | 140. | 1194. | Hála, Eyem, et al., 1970 | N2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | Squalane | 110. | 1136. | Hála, Eyem, et al., 1970 | N2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | Squalane | 125. | 1144. | Hála, Eyem, et al., 1970 | N2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | Squalane | 140. | 1154. | Hála, Eyem, et al., 1970 | N2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | SE-30 | 145. | 1151. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 160. | 1163. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 175. | 1174. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 190. | 1184. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Carbowax 20M | 145. | 1296. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | Carbowax 20M | 160. | 1310. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | Carbowax 20M | 175. | 1331. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Adamantyl siloxane | 160. | 1171. | Konstantinova, Berezkin, et al., 2005 | 22. m/0.22 mm/0.20 μm, Nitrogen |
Capillary | Adamantyl siloxane | 160. | 1171. | Konstantinova, Berezkin, et al., 2005, 2 | Nitrogen; Column length: 22. m; Column diameter: 0.22 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane | 1151. | Bayat and Abad, 2011 | Program: not specified |
Capillary | Polydimethyl siloxane | 1151. | Bayat and Abad M.F.Y., 2011 | Program: not specified |
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.
Anonymous, 1969
Anonymous, R.,
Freon Fluorocarbons - properties and applications, E. I. Du Pont, Freon Product Information, B-2, 1969. [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]
Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor pressure of acetophenone, (+-)-1,2-butanediol, (+-)-1,3-butanediol, diethylene glycol monopropyl ether, 1,3-dimethyladamantane, 2-ethoxyethyl acetate, ethyl octyl sufide, and pentyl acetate,
J. Chem. Eng. Data, 1996, 41, 1255-68. [all data]
Varushchenko, Pashchenko, et al., 2001
Varushchenko, R.M.; Pashchenko, L.L.; Druzhinina, A.I.; Abramenkov, A.V.; Pimersin, A.A.,
Thermodynamics of vaporization of some alkyladamantanes,
The Journal of Chemical Thermodynamics, 2001, 33, 7, 733-744, https://doi.org/10.1006/jcht.2000.0773
. [all data]
Steele, Chirico, et al., 1996, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure of Acetophenone, (±)-1,2-Butanediol, (±)-1,3-Butanediol, Diethylene Glycol Monopropyl Ether, 1,3-Dimethyladamantane, 2-Ethoxyethyl Acetate, Ethyl Octyl Sulfide, and Pentyl Acetate,
J. Chem. Eng. Data, 1996, 41, 6, 1255-1268, https://doi.org/10.1021/je9601117
. [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]
Varushchenko, Druzhinina, et al., 2005
Varushchenko, R.M.; Druzhinina, A.I.; Senyavin, V.M.; Sarkisova, V.S.,
The low-temperature heat capacities, phase transitions and thermodynamic properties of 1,3-dimethyladamantane and 1-ethyladamantane,
The Journal of Chemical Thermodynamics, 2005, 37, 2, 141-151, https://doi.org/10.1016/j.jct.2004.06.009
. [all data]
Arntz and Schneider, 1980
Arntz, Horst; Schneider, Gerhard M.,
Calorimetric investigations of plastic crystals at low temperatures and high pressures with differential scanning calorimetry,
Faraday Discuss. Chem. Soc., 1980, 69, 139, https://doi.org/10.1039/dc9806900139
. [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]
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]
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]
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.,
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]
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]
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, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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