Benzene, bromo-

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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
Δfliquid14.0kcal/molCmHolm, 1973Grignard Rx; ALS
Δfliquid14.55 ± 0.99kcal/molCmChernick, Skinner, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = 14.1 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-743.75 ± 0.16kcal/molCcbSmith and Bjellerup, 1947ALS
Quantity Value Units Method Reference Comment
liquid5239.5cal/mol*KN/AMasi and Scott, 1975DH
liquid49.69cal/mol*KN/AStull, 1937Extrapolation below 91 K, 55.86 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
37.26303.15Reddy, 1986T = 303.15, 313.15 K.; DH
36.876298.15Masi and Scott, 1975T = 11 to 300 K.; DH
37.139298.1Stull, 1937T = 90 to 320 K.; DH
34.80302.6de Kolossowsky and Udowenko, 1934DH
34.80302.6Kolosovskii and Udovenko, 1934DH
30.50231.7Andrews and Haworth, 1928T = 101 to 232 K. Value is unsmoothed experimental datum.; DH
36.21293.2Williams and Daniels, 1925T = 20 to 80°C.; DH
36.09298.von Reis, 1881T = 291 to 444 K.; DH

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
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
Tboil429.1 ± 0.6KAVGN/AAverage of 27 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus242.4 ± 0.3KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple242.42KN/AMarsh, 1987Uncertainty assigned by TRC = 0.02 K; recommended as fixed point for thermometry; TRC
Ttriple242.400KN/AMasi and Scott, 1975, 2Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple242.4KN/AStull, 1937, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δvap10.65kcal/molN/AMajer and Svoboda, 1985 
Δvap10.7kcal/molN/ABoublik, Fried, et al., 1984Based on data from 330. - 430. K. See also Basarová and Svoboda, 1991.; AC
Δvap10.6 ± 0.02kcal/molCWadsö, Luoma, et al., 1968AC
Δvap10.65 ± 0.01kcal/molCWadso, 1968ALS
Δvap9.05 ± 0.008kcal/molVMathews, 1926ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
300.90.007Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
10.1348.AStephenson and Malanowski, 1987Based on data from 333. - 463. K. See also Dykyj, 1972.; AC
10.5293.CMasi and Scott, 1975, 3AC
10.1344.N/ADreyer, Martin, et al., 1955Based on data from 329. - 427. K.; 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
329.22 - 427.394.066311495.044-61.508Dreyer, Martin, et al., 1955Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.5578242.40Masi and Scott, 1975DH
2.56242.4Domalski and Hearing, 1996AC
2.5399242.43Stull, 1937DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
10.55242.40Masi and Scott, 1975DH
10.48242.43Stull, 1937DH

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
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

C6H4Br- + Hydrogen cation = Benzene, bromo-

By formula: C6H4Br- + H+ = C6H5Br

Quantity Value Units Method Reference Comment
Δr387.2 ± 2.5kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Δr384.0 ± 2.1kcal/molG+TSLinnert and Riveros, 1994gas phase; Acidity between quinoline and benzonitrile; B
Quantity Value Units Method Reference Comment
Δr379.0 ± 2.6kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Δr375.8 ± 2.0kcal/molIMRBLinnert and Riveros, 1994gas phase; Acidity between quinoline and benzonitrile; B

C6H7N+ + Benzene, bromo- = (C6H7N+ • Benzene, bromo-)

By formula: C6H7N+ + C6H5Br = (C6H7N+ • C6H5Br)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr13.6kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
5.1325.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C6H4Br- + Hydrogen cation = Benzene, bromo-

By formula: C6H4Br- + H+ = C6H5Br

Quantity Value Units Method Reference Comment
Δr383.5 ± 2.1kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Δr375.3 ± 2.2kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C6H4Br- + Hydrogen cation = Benzene, bromo-

By formula: C6H4Br- + H+ = C6H5Br

Quantity Value Units Method Reference Comment
Δr392.8 ± 2.0kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Δr385.0 ± 2.1kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

Ethylbenzene + Benzene, bromo- = C8H9Br + Benzene

By formula: C8H10 + C6H5Br = C8H9Br + C6H6

Quantity Value Units Method Reference Comment
Δr-0.14 ± 0.0050kcal/molCmMerdzhanov, Alenin, et al., 1982gas phase; Heat of isomerization at 349 K; ALS

2Benzene, bromo- + Mercury(II) bromide = Mercury, diphenyl- + 2Bromine

By formula: 2C6H5Br + Br2Hg = C12H10Hg + 2Br2

Quantity Value Units Method Reference Comment
Δr78.53 ± 0.80kcal/molCmChernick, Skinner, et al., 1956liquid phase; ALS

Chlorine anion + Benzene, bromo- = (Chlorine anion • Benzene, bromo-)

By formula: Cl- + C6H5Br = (Cl- • C6H5Br)

Quantity Value Units Method Reference Comment
Δr6.80kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B,M

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, 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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Mass 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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291408

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References

Go To: Top, 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.

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]

Chernick, Skinner, et al., 1956
Chernick, C.L.; Skinner, H.A.; Wadso, I., Thermochemistry of metallic alkyls. Part 7.-The heat of formation of mercury diphenyl, and of mercury phenyl chloride, Trans. Faraday Soc., 1956, 52, 1088-1093. [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]

Smith and Bjellerup, 1947
Smith, L.; Bjellerup, L., Neue Versuche mit beweglicher calorimetrischer Bombe, Acta Chem. Scand., 1947, 1, 566-570. [all data]

Masi and Scott, 1975
Masi, J.F.; Scott, R.B., Some thermodynamic properties of bromobenzene from 0 to 1500K, J. Res., 1975, NBS 79A, 619-628. [all data]

Stull, 1937
Stull, D.R., A semi-micro calorimeter for measuring heat capacities at low temperatures, J. Am. Chem. Soc., 1937, 59, 2726-2733. [all data]

Reddy, 1986
Reddy, K.S., Isentropic compressibilities of binary liquid mixtures at 303.15 and 313.15 K, J. Chem. Eng. Data, 1986, 31, 238-240. [all data]

de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W., Determination des chaleurs specifiques des liquides, Compt. rend., 1934, 198, 1394-1395. [all data]

Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W., Specific heat of liquids. II., Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]

Andrews and Haworth, 1928
Andrews, D.H.; Haworth, E., An application of the rule of Dulong and Petit to molecules, J. Am. Chem. Soc., 1928, 50, 2998-3002. [all data]

Williams and Daniels, 1925
Williams, J.W.; Daniels, F., The specific heats of binary mixtures, J. Am. Chem. Soc., 1925, 47, 1490-1503. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Marsh, 1987
Marsh, K.N., Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Sci. Pub., Oxford, 1987. [all data]

Masi and Scott, 1975, 2
Masi, J.F.; Scott, R.B., Some thermodynamic properties of bromobenzene from 0 to 1500k, J. Res. Natl. Bur. Stand., Sect. A, 1975, 79, 619-28. [all data]

Stull, 1937, 2
Stull, D.R., A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp., J. Am. Chem. Soc., 1937, 59, 2726. [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]

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]

Mathews, 1926
Mathews, J.H., The accurate measurement of heats of vaporization of liquids, J. Am. Chem. Soc., 1926, 48, 562-576. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Masi and Scott, 1975, 3
Masi, Joseph F.; Scott, Russell B., Some thermodynamic properties of bromobenzene from 0 to 1500 K, J. RES. NATL. BUR. STAN. SECT. A., 1975, 79A, 5, 619, https://doi.org/10.6028/jres.079A.022 . [all data]

Dreyer, Martin, et al., 1955
Dreyer, R.; Martin, W.; von Weber, U., Die S«65533»ttigungsdampfdrucke von Benzol, Toluol, «65533»thylbenzol, Styrol, Cumol und Brombenzol zwischen 10 und 760 Torr, J. Prakt. Chem., 1955, 1, 5-6, 324-328, https://doi.org/10.1002/prac.19550010508 . [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]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [all data]

Linnert and Riveros, 1994
Linnert, H.V.; Riveros, J.M., Benzyne-related mechanisms in the gas phase ion molecule reactions of haloarenes, Int. J. Mass Spectrom. Ion Proc., 1994, 140, 1, 163, https://doi.org/10.1016/0168-1176(94)04079-6 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Merdzhanov, Alenin, et al., 1982
Merdzhanov, V.R.; Alenin, V.I.; Nesterova, T.N.; Rozhnov, A.M., Study of equilibrium transformation of ethylbromobenzenes, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1982, 25, 1047-1049. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]


Notes

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