1-Bromoadamantane
- Formula: C10H15Br
- Molecular weight: 215.130
- 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, IR Spectrum, 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
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, IR Spectrum, 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:
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 |
IR Spectrum
Go To: Top, Phase change data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Download spectrum in JCAMP-DX format.
Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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 |
---|---|---|---|---|---|
Packed | SE-30 | 150. | 1389. | L'vova, Kurbatova, et al., 2001 | N2, N-AW Chromaton; Column length: 1. m |
Packed | SE-30 | 150. | 1389. | Yashkin, Kurbatova, et al., 2001 | CHromaton N-AW; Column length: 1. m |
Capillary | SE-30 | 145. | 1382. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 160. | 1403. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 175. | 1419. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | SE-30 | 190. | 1436. | 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 | 150. | 1817. | L'vova, Kurbatova, et al., 2001 | N2, N-AW Chromaton; Column length: 1. m |
Packed | Carbowax 20M | 150. | 1817. | Yashkin, Kurbatova, et al., 2001 | Column length: 1. m |
Capillary | Carbowax 20M | 145. | 1809. | Burkhard, Vais, et al., 1969 | N2; Column length: 50. m; Column diameter: 0.27 mm |
Capillary | Carbowax 20M | 160. | 1837. | 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. | 1386. | Konstantinova, Berezkin, et al., 2005 | 22. m/0.22 mm/0.20 μm, Nitrogen |
Capillary | Adamantyl siloxane | 160. | 1386. | 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 | 1382. | Bayat and Abad, 2011 | Program: not specified |
Capillary | Polydimethyl siloxane | 1382. | Bayat and Abad M.F.Y., 2011 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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., 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]
L'vova, Kurbatova, et al., 2001
L'vova, N.Yu.; Kurbatova, S.V.; Yashkin, S.N.; Kolosova, E.A.,
Gas chromatography of halogenated adamantanes,
Russ. J. Phys. Chem. (Engl. Transl.), 2001, 75, 12, 2053-2056. [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]
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, IR Spectrum, Gas Chromatography, 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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