Adamantan-1-carboxylic acid, methyl ester
- Formula: C12H18O2
- Molecular weight: 194.2701
- IUPAC Standard InChIKey: CLYOOVNORYNXMD-UHFFFAOYSA-N
- CAS Registry Number: 711-01-3
- 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: Adamantane-1-carboxylic acid, methyl ester; 1-Adamantanecarboxylic acid, methyl ester; Tricyclo[3.3.1.13,7]decane-1-carboxylic acid, methyl ester
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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 |
---|---|---|---|---|---|
ΔfH°gas | -118.4 ± 0.65 | kcal/mol | Ccb | Abboud, Jimenez, et al., 1992 |
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔsubH° | 19.7 ± 0.1 | kcal/mol | V | Abboud, Jimenez, et al., 1992 | ALS |
ΔsubH° | 19.7 | kcal/mol | N/A | Abboud, Jimenez, et al., 1992 | DRB |
ΔsubH° | 19.7 ± 0.1 | kcal/mol | N/A | Abboud, Jimenez, et al., 1992 | AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.1 ± 0.1 | 275. | ME | Abboud, Jimenez, et al., 1992 | Based on data from 267. to 283. K.; AC |
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:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 206.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 199.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.38 ± 0.03 | PE | Miller, Koch, et al., 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C10H15+ | 10. ± 0.2 | COOCH3 | PI | Zauer and Takhistov, 1986 | LBLHLM |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 200. | 1489. | Suslov, Rudenko, et al., 1988 | N2; Column length: 50. m; Column diameter: 0.25 mm |
Packed | SE-30 | 140. | 1431. | Heintz, Gruselle, et al., 1976 | Chromosorb W (60-80 mesh); Column length: 2. m |
Capillary | SE-30 | 145. | 1449. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 160. | 1465. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 175. | 1474. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 190. | 1486. | 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 |
---|---|---|---|---|---|
Packed | Carbowax 20M | 140. | 1858. | Heintz, Gruselle, et al., 1976 | Chromosorb W (60-80 mesh); Column length: 2. m |
Capillary | Carbowax 20M | 145. | 1892. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | Carbowax 20M | 160. | 1914. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | Carbowax 20M | 175. | 1937. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
References
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Abboud, Jimenez, et al., 1992
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.,
Structural effects on the thermochemical properties of organic compounds. III. Enthalpies of combustion, vapour pressures and enthalpies of sublimation, and standard enthalpies of formation in the gaseous phase, of adamantane-1-carboxylic acid methyl ester and of adamantane-1-carbonitrile,
J. Chem. Thermodyn., 1992, 24, 1299-1304. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [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]
Zauer and Takhistov, 1986
Zauer, O.A.; Takhistov, V.V.,
Heats of formation of 1-adamantyl cations in the gas phase,
J. Org. Chem. USSR, 1986, 22, 601. [all data]
Suslov, Rudenko, et al., 1988
Suslov, I.A.; Rudenko, B.A.; Arzamastsev, A.P.,
Capillary chromatography of adamantane derivatives,
Zh. Anal. Khim., 1988, 43, 328-332. [all data]
Heintz, Gruselle, et al., 1976
Heintz, M.; Gruselle, M.; Druilhe, A.; Lefort, D.,
Relations entre structure chimique et données de rétention en chromatographie en phase gaseuse. VI. Alcools et esters méthyliques de structures cycliques,
Chromatographia, 1976, 9, 8, 367-372, https://doi.org/10.1007/BF02330385
. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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