1-Bromoadamantane
- Formula: C10H15Br
- Molecular weight: 215.130
- IUPAC Standard InChI: InChI=1S/C10H15Br/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
- IUPAC Standard InChIKey: VQHPRVYDKRESCL-UHFFFAOYSA-N
- CAS Registry Number: 768-90-1
- 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-bromo-; Adamantane, 1-bromo-; Adamantyl bromide; 1-Adamantyl bromide; 1-bromotricyclo[3.3.1.13,7]decane
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Phase change data
Go To: Top, 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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 | 396.5 | K | N/A | Clark, Knox, et al., 1977 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 0.949 | 391.8 | DSC | Bazyleva, Blokhin, et al., 2005 | Based on data from 290. to 430. K.; AC |
| 0.915 | 396.5 | N/A | Clark, Knox, et al., 1977 | AC |
Entropy of fusion
| ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 0.753 | 279. | Clark, Knox, et al., 1977 | CAL |
| 5.335 | 310.5 | ||
| 2.31 | 396.5 |
Gas phase ion energetics data
Go To: Top, Phase change 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 as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.4 | PE | Abeywickrema, Della, et al., 1984 | LBLHLM |
| 9.30 ± 0.06 | PE | Worley, Mateescu, et al., 1973 | LLK |
| 9.2 | PE | Mateescu and Workey, 1972 | LLK |
| 9.63 ± 0.01 | PE | Abeywickrema, Della, et al., 1984 | Vertical value; LBLHLM |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C10H15+ | 9.3 ± 0.2 | Br | PI | Zauer and Takhistov, 1986 | LBLHLM |
References
Go To: Top, Phase change data, Gas phase ion energetics data, 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., 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]
Bazyleva, Blokhin, et al., 2005
Bazyleva, Ala B.; Blokhin, Andrey V.; Kabo, Gennady J.; Kabo, Andrey G.; Paulechka, Yauheni U.,
Thermodynamic properties of 1-bromoadamantane in the condensed state and molecular disorder in its crystals,
The Journal of Chemical Thermodynamics, 2005, 37, 7, 643-657, https://doi.org/10.1016/j.jct.2004.10.005
. [all data]
Abeywickrema, Della, et al., 1984
Abeywickrema, R.S.; Della, E.W.; Pigou, P.E.; Livett, M.K.; Peel, J.B.,
Orbital interactions in some polycycloalkyl halides: A photoelectron spectroscopic study,
J. Am. Chem. Soc., 1984, 106, 7321. [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]
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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