Propane, 2-bromo-2-methyl-
- Formula: C4H9Br
- Molecular weight: 137.018
- IUPAC Standard InChI: InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3
- 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
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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 | -31.64 ± 0.37 | kcal/mol | Eqk | Howlett, 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -30.48 kcal/mol |
Reaction 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
= (
•
)
By formula: Br- + C4H9Br = (Br- • C4H9Br)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.6 ± 1.0 | kcal/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
| ΔrH° | 12.40 | kcal/mol | TDAs | Dougherty, 1974 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 19.3 | cal/mol*K | HPMS | Dougherty, 1974 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 7.30 ± 0.20 | kcal/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
| ΔrG° | 6.70 | kcal/mol | TDAs | Dougherty, 1974 | gas phase; B |
+
= (
•
)
By formula: F- + C4H9Br = (F- • C4H9Br)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 22.3 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1983 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 15.3 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1983 | gas phase; B |
+
= (
•
)
By formula: Cl- + C4H9Br = (Cl- • C4H9Br)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.7 ± 1.0 | kcal/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 8.90 ± 0.20 | kcal/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
+
= (
•
)
By formula: Na+ + C4H9Br = (Na+ • C4H9Br)
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 13.7 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
=
+
By formula: C4H9Br = C4H8 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 18.9 ± 0.9 | kcal/mol | Eqk | Kistiakowsky and Stauffer, 1937 | gas phase; ALS |
+
=
By formula: HBr + C4H8 = C4H9Br
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -18.850 | kcal/mol | Eqk | Howlett, 1957 | gas phase; ALS |
=
By formula: C4H9Br = C4H9Br
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 4.54 | kcal/mol | Eqk | Nesterova and Rozhnov, 1974 | gas phase; ALS |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- GAS; PERKIN-ELMER 21 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY (ADJUSTED addcm-115-12-3); 2 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1340, AND 10% IN CS2 FOR 1340-430 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
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 |
|---|---|---|---|---|---|
| Packed | Squalane | 27. | 595. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 49. | 600. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 67. | 603. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Apiezon L | 130. | 632. | von Kováts, 1958 | Celite (40:60 Gewichtsverhaltnis) |
| Packed | Apiezon L | 70. | 619. | von Kováts, 1958 | Celite (40:60 Gewichtsverhaltnis) |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-54 | 623. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Normal alkane RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | Apiezon L | 130. | 633. | Arruda, Junkes, et al., 2008 |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Methyl Silicone | 615. | Zenkevich and Marinichev, 2001 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
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]
Li, Ross, et al., 1996
Li, C.; Ross, P.; Szulejko, J.; McMahon, T.B.,
High-Pressure Mass Spectrometric Investigations of the Potential Energy Surfaces of Gas-Phase Sn2 Reactions.,
J. Am. Chem. Soc., 1996, 118, 39, 9360, https://doi.org/10.1021/ja960565o
. [all data]
Dougherty, 1974
Dougherty, R.C.,
SN2 reactions in the gas phase. Alkyl group structural effects,
Org. Mass Spectrom., 1974, 8, 85. [all data]
Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B.,
Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements,
J. Am. Chem. Soc., 1983, 105, 2944. [all data]
McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G.,
An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions,
Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7
. [all data]
Kistiakowsky and Stauffer, 1937
Kistiakowsky, G.B.; Stauffer, C.H.,
The kinetics of gaseous addition of halogen acids to isobutene, 1937, 165-170. [all data]
Nesterova and Rozhnov, 1974
Nesterova, T.N.; Rozhnov, A.M.,
Isomerization of isostructural monobromobutanes,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1974, 17, 556-558. [all data]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
von Kováts, 1958
von Kováts, E.,
206. Gas-chromatographische Charakterisierung organischer Verbindungen. Teil 1: Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde und Ketone,
Helv. Chim. Acta, 1958, 41, 7, 1915-1932, https://doi.org/10.1002/hlca.19580410703
. [all data]
Weber, 1986
Weber, L.,
Utilization of the Sadtler standard RI system in micropollution analyses,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 446-451, https://doi.org/10.1002/jhrc.1240090806
. [all data]
Arruda, Junkes, et al., 2008
Arruda, A.C.S.; Junkes, B. da.S.; Souza, E.S.; Yunes, R.A.; Heizen, V.E.F.,
Semi-Emlirical Topological Index to Predict Properties of Halogenated Aliphatic Compounds,
J. Chemometrics, 2008, 22, 3-4, 186-194, https://doi.org/10.1002/cem.1121
. [all data]
Zenkevich and Marinichev, 2001
Zenkevich, I.G.; Marinichev, A.N.,
Comparison of Topological and Dynamics Molecular Characteristics for Precalculation of Chromatographic Retention Parameters of Organic Compounds (in Russian),
Zh. Struct. Khim., 2001, 42, 5, 893-902. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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