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Propane, 2-bromo-2-methyl-

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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
Deltafgas-31.64 ± 0.37kcal/molEqkHowlett, 1957Reanalyzed by Cox and Pilcher, 1970, Original value = -30.48 kcal/mol

Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-31.89kcal/molEqkNesterova and Rozhnov, 1974ALS
Deltafliquid-39.2kcal/molCmHolm, 1973Grignard Rx; ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
39.60298.15Shehatta, 1993DH

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:
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
Tboil346.4KN/AWeast and Grasselli, 1989BS
Tboil348.KN/AAmerican Tokyo Kasei, 1988BS
Tboil346.4KN/AMajer and Svoboda, 1985 
Tboil346.KN/AKornblum, Smiley, et al., 1955Uncertainty assigned by TRC = 2. K; TRC
Tboil346.1KN/AKushner, Crowe, et al., 1950Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tfus256.95KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.4 K; TRC
Tfus256.2KN/AKushner, Crowe, et al., 1950Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Tfus146.KN/ATimmermans, 1935Uncertainty assigned by TRC = 3. K; TRC
Tfus246.05KN/ATimmermans, 1934Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Deltavap7.631kcal/molN/AMajer and Svoboda, 1985 
Deltavap7.4kcal/molN/ABoublik, Fried, et al., 1984Based on data from 270. - 345. K. See also Basarová and Svoboda, 1991.; AC
Deltavap7.60 ± 0.02kcal/molCWadsö, Luoma, et al., 1968AC
Deltavap7.603 ± 0.029kcal/molCWadso, 1968ALS
Deltavap7.40 ± 0.20kcal/molVBryce-Smith and Howlett, 1951ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
6.986346.4N/AMajer and Svoboda, 1985 
7.50263.AStephenson and Malanowski, 1987Based on data from 248. - 346. K.; AC
7.53313.N/ACalero, Valle, et al., 1969Based on data from 298. - 323. K.; AC
7.46288.N/AHull, Campbell, et al., 1951Based on data from 273. - 346. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
273. - 346.04.558741539.717-8.195Bryce-Smith and Howlett, 1951, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
0.471256.1Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
6.472208.6Domalski and Hearing, 1996CAL
1.08231.5
1.84256.1

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Bromine anion + Propane, 2-bromo-2-methyl- = (Bromine anion bullet Propane, 2-bromo-2-methyl-)

By formula: Br- + C4H9Br = (Br- bullet C4H9Br)

Quantity Value Units Method Reference Comment
Deltar15.6 ± 1.0kcal/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar12.40kcal/molTDAsDougherty, 1974gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar19.3cal/mol*KHPMSDougherty, 1974gas phase; M
Quantity Value Units Method Reference Comment
Deltar7.30 ± 0.20kcal/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar6.70kcal/molTDAsDougherty, 1974gas phase; B

Fluorine anion + Propane, 2-bromo-2-methyl- = (Fluorine anion bullet Propane, 2-bromo-2-methyl-)

By formula: F- + C4H9Br = (F- bullet C4H9Br)

Quantity Value Units Method Reference Comment
Deltar22.3 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B
Quantity Value Units Method Reference Comment
Deltar15.3 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B

Chlorine anion + Propane, 2-bromo-2-methyl- = (Chlorine anion bullet Propane, 2-bromo-2-methyl-)

By formula: Cl- + C4H9Br = (Cl- bullet C4H9Br)

Quantity Value Units Method Reference Comment
Deltar17.7 ± 1.0kcal/molTDAsLi, Ross, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar8.90 ± 0.20kcal/molTDAsLi, Ross, et al., 1996gas phase; B

Sodium ion (1+) + Propane, 2-bromo-2-methyl- = (Sodium ion (1+) bullet Propane, 2-bromo-2-methyl-)

By formula: Na+ + C4H9Br = (Na+ bullet C4H9Br)

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
13.7298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

Propane, 2-bromo-2-methyl- = 1-Propene, 2-methyl- + Hydrogen chloride

By formula: C4H9Br = C4H8 + HCl

Quantity Value Units Method Reference Comment
Deltar18.9 ± 0.9kcal/molEqkKistiakowsky and Stauffer, 1937gas phase; ALS

Hydrogen bromide + 1-Propene, 2-methyl- = Propane, 2-bromo-2-methyl-

By formula: HBr + C4H8 = C4H9Br

Quantity Value Units Method Reference Comment
Deltar-18.850kcal/molEqkHowlett, 1957gas phase; ALS

Propane, 2-bromo-2-methyl- = Propane, 1-bromo-2-methyl-

By formula: C4H9Br = C4H9Br

Quantity Value Units Method Reference Comment
Deltar4.54kcal/molEqkNesterova and Rozhnov, 1974gas phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-1604
NIST MS number 227729

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

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]

Holm, 1973
Holm, T., Thermochemistry of Grignard reagents. Enthalpies of formation of alkylmagnesium bromides and of alkyl bromides, J. Organomet. Chem., 1973, 56, 87-93. [all data]

Shehatta, 1993
Shehatta, I., Heat capacity at constant pressure of some halogen compounds, Thermochim. Acta, 1993, 213, 1-10. [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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References