Propane, 2-bromo-2-methyl-
- Formula: C4H9Br
- Molecular weight: 137.018
- IUPAC Standard InChIKey: RKSOPLXZQNSWAS-UHFFFAOYSA-N
- CAS Registry Number: 507-19-7
- 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: tert-Butyl bromide; Trimethylbromomethane; 2-Bromo-2-methylpropane; 2-Bromoisobutane; tert-C4H9Br; t-Butyl bromide; Bromotrimethylmethane; Tertiarybutyl bromide; Butylbromide, tert-; 1,1-Dimethylethyl bromide; 2-Methyl-2-bromopropane; NSC 8418
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Gas phase thermochemistry data
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -132.4 ± 1.5 | kJ/mol | Eqk | Howlett, 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -127.5 kJ/mol |
Phase change data
Go To: Top, Gas phase thermochemistry 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
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
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 | 346.4 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 348. | K | N/A | American Tokyo Kasei, 1988 | BS |
Tboil | 346.4 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 346. | K | N/A | Kornblum, Smiley, et al., 1955 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 346.1 | K | N/A | Kushner, Crowe, et al., 1950 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 256.95 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 256.2 | K | N/A | Kushner, Crowe, et al., 1950 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 146. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 246.05 | K | N/A | Timmermans, 1934 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 31.93 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 31. | kJ/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 270. to 345. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 31.8 ± 0.1 | kJ/mol | C | Wadsö, Luoma, et al., 1968 | AC |
ΔvapH° | 31.81 ± 0.12 | kJ/mol | C | Wadso, 1968 | ALS |
ΔvapH° | 31.0 ± 0.84 | kJ/mol | V | Bryce-Smith and Howlett, 1951 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
29.23 | 346.4 | N/A | Majer and Svoboda, 1985 | |
31.4 | 263. | A | Stephenson and Malanowski, 1987 | Based on data from 248. to 346. K.; AC |
31.5 | 313. | N/A | Calero, Valle, et al., 1969 | Based on data from 298. to 323. K.; AC |
31.2 | 288. | N/A | Hull, Campbell, et al., 1951 | Based on data from 273. to 346. K. See also Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
273. to 346.0 | 4.56445 | 1539.717 | -8.195 | Bryce-Smith and Howlett, 1951, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.97 | 256.1 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
27.08 | 208.6 | Domalski and Hearing, 1996 | CAL |
4.52 | 231.5 | ||
7.68 | 256.1 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.92 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.95 | EST | Luo and Pacey, 1992 | LL |
9.95 ± 0.015 | PE | Hashmall and Heilbronner, 1970 | RDSH |
9.89 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.95 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.05 | PE | Flamini, Semprini, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H9+ | 9.85 ± 0.01 | Br | PI | McLoughlin and Traeger, 1979 | LLK |
References
Go To: Top, Gas phase thermochemistry data, 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.
Howlett, 1957
Howlett, K.E.,
The use of equilibrium constants to calculate thermodynamic quantities. Part III. Equilibria in the system tert.-butyl bromideisobutene-hydrogen bromide,
J. Chem. Soc., 1957, 2834-2836. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
American Tokyo Kasei, 1988
American Tokyo Kasei,
TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Kornblum, Smiley, et al., 1955
Kornblum, N.; Smiley, R.A.; Ungnade, H.E.; White, A.M.; Taub, B.,
The reaction of silver nitrite with secondary and tertiary alkyl halides,
J. Am. Chem. Soc., 1955, 77, 5528-33. [all data]
Kushner, Crowe, et al., 1950
Kushner, L.M.; Crowe, R.W.; Smyth, C.P.,
The Heat Capacity and Dielectric Constants of Some Alkyl Halides in the Solid State,
J. Am. Chem. Soc., 1950, 72, 1091. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Timmermans, 1934
Timmermans, J.,
Theory of Concentrated Solutions XII.,
Bull. Soc. Chim. Belg., 1934, 43, 626. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav,
Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data,
Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I
. [all data]
Wadsö, Luoma, et al., 1968
Wadsö, Ingemar; Luoma, Sinikka; Olson, Thomas; Norin, Torbjörn,
Heats of Vaporization of Organic Compounds. II. Chlorides, Bromides, and Iodides.,
Acta Chem. Scand., 1968, 22, 2438-2444, https://doi.org/10.3891/acta.chem.scand.22-2438
. [all data]
Wadso, 1968
Wadso, I.,
Heats of vaporization of organic compounds II. Chlorides, bromides, and iodides,
Acta Chem. Scand., 1968, 22, 2438. [all data]
Bryce-Smith and Howlett, 1951
Bryce-Smith, D.; Howlett, K.E.,
The preparation and properties of tert-butyl bromide,
J. Chem. Soc., 1951, 1141-11. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Calero, Valle, et al., 1969
Calero, G.C.; Valle, M.M.; Losa, C.G.,
Rev. Acad. Cienc. Fis. Quim. Nat. Zaragoza, 1969, 24, 2, 137. [all data]
Hull, Campbell, et al., 1951
Hull, R.; Campbell, Neil; Stafford, W.H.; Wilshire, J.F.K.; Briggs, Lindsay H.; Nicholls, G.A.; Johnson, A.W.; Sheppard, N.; Todd, A.R.; Ratcliffe, J.; Bryce-Smith, D.; Howlett, K.E.; Groves, L.H.; Swan, G.A.,
Notes,
J. Chem. Soc., 1951, 1136, https://doi.org/10.1039/jr9510001136
. [all data]
Bryce-Smith and Howlett, 1951, 2
Bryce-Smith, D.; Howlett, K.E.,
The Preparation and Properties of tert.-Butyl Bromide,
J. Chem. Soc., 1951, 1141-1142. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D.,
Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes,
Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]
Hashmall and Heilbronner, 1970
Hashmall, J.A.; Heilbronner, E.,
n-Ionization potentials of alkyl bromides,
Angew. Chem. Intern. Ed., 1970, 9, 305. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Flamini, Semprini, et al., 1976
Flamini, A.; Semprini, E.; Stefani, F.; Sorriso, S.; Cardaci, G.,
He(I) photoelectron spectra and semiempirical molecular-orbital calculations on methylmetal halides of group 4A elements,
J. Chem. Soc. Dalton Trans., 1976, 731. [all data]
McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C.,
Heat of formation for tert-butyl cation in the gas phase,
J. Am. Chem. Soc., 1979, 101, 5791. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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