Benzene, 1,4-dibromo-
- Formula: C6H4Br2
- Molecular weight: 235.904
- IUPAC Standard InChIKey: SWJPEBQEEAHIGZ-UHFFFAOYSA-N
- CAS Registry Number: 106-37-6
- 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: Benzene, p-dibromo-; p-Bromophenyl bromide; p-Dibromobenzene; 1,4-Dibromobenzene; Dibromobenzene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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 |
---|---|---|---|---|---|
ΔcH°solid | -703.182 | kcal/mol | Ccb | Popoff and Schirokich, 1933 | At 288 °K; ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.80 | 198.15 | Ueberreiter and Orthmann, 1950 | T = 293 to 368 K. Equation only.; DH |
41.71 | 299.8 | Andrews and Haworth, 1928 | T = 101 to 336 K. Value is unsmoothed experimental datum.; 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 491.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 493.55 | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.07 K; TRC |
Tboil | 493.4 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tboil | 493.4 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 360. ± 3. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 17.74 ± 0.026 | kcal/mol | ME | Oonk, van Genderen, et al., 2000 | AC |
ΔsubH° | 14.3 | kcal/mol | ME,GS | Zibberman-Granovskaya, 1940 | Based on data from 248. to 303. K. See also Jones, 1960.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.9 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 493. K. See also Dykyj, 1972.; 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 |
---|---|---|---|---|---|
334. to 491.8 | 2.48272 | 757.96 | -191.23 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
17.5 | 313. | N/A | Stephenson and Malanowski, 1987 | Based on data from 298. to 354. K.; AC |
17.5 ± 0.1 | 326. | V | Walsh and Smith, 1961 | ALS |
17.5 ± 0.1 | 326. | N/A | Walsh and Smith, 1961, 2 | Based on data from 278. to 353. K.; AC |
17.6 | 288. | N/A | Stern and Gregory, 1959 | Based on data from 228. to 347. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.873 | 360.5 | Kuramochi, Maeda, et al., 2004 | See also van der Linde, van Miltenburg, et al., 2005.; AC |
4.790 | 360.1 | Acree, 1991 | AC |
4.7897 | 360. | Ueberreiter and Orthmann, 1950 | DH |
4.9068 | 360.05 | Narbutt, 1918 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.3 | 360. | Ueberreiter and Orthmann, 1950 | DH |
13.6 | 360.05 | Narbutt, 1918 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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:
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.82 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°(+) ion | 234. | kcal/mol | N/A | N/A | |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH(+) ion,0K | 240. | kcal/mol | N/A | N/A |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.82 ± 0.02 | PIPECO | Olesik, Baer, et al., 1986 | LBLHLM |
8.85 ± 0.02 | PI | Moini and Leroi, 1986 | LBLHLM |
8.8 | PE | Kimura, Katsumata, et al., 1981 | LLK |
8.9 ± 0.15 | CTS | Voigt and Reid, 1964 | RDSH |
8.90 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
8.909 | PE | Potts, Lyus, et al., 1980 | Vertical value; LLK |
8.90 ± 0.03 | PE | Cvitas and Klasinc, 1977 | Vertical value; LLK |
8.91 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
8.97 | PE | Baker, May, et al., 1968 | Vertical value; RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H4+ | 12.3 ± 0.1 | Br2 | PI | Moini and Leroi, 1986 | LBLHLM |
C6H4Br+ | 12.17 ± 0.05 | Br | PI | Moini and Leroi, 1986 | LBLHLM |
Mass spectrum (electron ionization)
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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
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 | Chuck Anderson, Aldrich Chemical Co. |
NIST MS number | 107690 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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.
Popoff and Schirokich, 1933
Popoff, M.M.; Schirokich, P.K.,
Ein Calorimeter zum Verbrennen von Chlor- und Bromderivaten,
Z. Phys. Chem. (Leipzig), 1933, 167, 183-187. [all data]
Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J.,
Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme,
Z. Natursforsch. 5a, 1950, 101-108. [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]
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]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 2875-8. [all data]
Lecat, 1947
Lecat, M.,
Some azeotropes of which one constituant is heterocyclic nitrogen,
Ann. Soc. Sci. Bruxelles, Ser. 1, 1947, 61, 73. [all data]
Lecat, 1943
Lecat, M.,
Azeotropes of Ethyl Urethane and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]
Oonk, van Genderen, et al., 2000
Oonk, Harry A.J.; van Genderen, Aad C.G.; Blok, Jacobus G.; van der Linde, Peter R.,
Vapour pressures of crystalline and liquid 1,4-dibromo- and 1,4-dichlorobenzene; lattice energies of 1,4-dihalobenzenes,
Phys. Chem. Chem. Phys., 2000, 2, 24, 5614-5618, https://doi.org/10.1039/b005324o
. [all data]
Zibberman-Granovskaya, 1940
Zibberman-Granovskaya, A.A.,
Russ. J. Phys. Chem., 1940, 14, 759. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Walsh and Smith, 1961
Walsh, P.N.; Smith, N.O.,
Sublimation pressure of a-p-dichloro-,β-p-dichloro-, p-dibromo-, and p-bromochlorobenzene,
J. Chem. Eng. Data, 1961, 6, 33. [all data]
Walsh and Smith, 1961, 2
Walsh, P.N.; Smith, N.O.,
Sublimation Pressure of α-p-Dichloro-β-p-Dichloro, and p-Dibromo-, and p-Bromochlorobenzene.,
J. Chem. Eng. Data, 1961, 6, 1, 33-35, https://doi.org/10.1021/je60009a010
. [all data]
Stern and Gregory, 1959
Stern, J.H.; Gregory, N.W.,
Vaporization Characteristics of p-Dibromobenzene,
J. Phys. Chem., 1959, 63, 4, 556-559, https://doi.org/10.1021/j150574a026
. [all data]
Kuramochi, Maeda, et al., 2004
Kuramochi, Hidetoshi; Maeda, Kouji; Kawamoto, Katsuya,
Measurements of Water Solubilities and 1-Octanol/Water Partition Coefficients and Estimations of Henry's Law Constants for Brominated Benzenes,
J. Chem. Eng. Data, 2004, 49, 3, 720-724, https://doi.org/10.1021/je0342724
. [all data]
van der Linde, van Miltenburg, et al., 2005
van der Linde, Peter R.; van Miltenburg, J. Cees; van den Berg, Gerrit J.K.; Oonk, Harry A.J.,
Low-Temperature Heat Capacities and Derived Thermodynamic Functions of 1,4-Dichlorobenzene, 1,4-Dibromobenzene, 1,3,5-Trichlorobenzene, and 1,3,5-Tribromobenzene,
J. Chem. Eng. Data, 2005, 50, 1, 164-172, https://doi.org/10.1021/je049762q
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Narbutt, 1918
Narbutt, J.,
Die Spezifischen Warmen und Schmelzwarmen der dichloro-, chlorbrom-, dibrom-, bromjod-, und dijodbenzole. I,
Z. Elektrochem., 1918, 24, 339-342. [all data]
Olesik, Baer, et al., 1986
Olesik, S.; Baer, T.; Morrow, J.C.,
Dissociation rates of energy-selected dichloro- and dibromobenzene ions,
J. Phys. Chem., 1986, 90, 3563. [all data]
Moini and Leroi, 1986
Moini, M.; Leroi, G.E.,
Photoionization and fragmentation of o-, m- and p-dibromobenzene: Isomer scrambling and product thermochemistry,
J. Phys. Chem., 1986, 90, 4002. [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]
Voigt and Reid, 1964
Voigt, E.M.; Reid, C.,
Ionization potentials of substituted benzenes and their charge-transfer spectra with tetracyanoethylene,
J. Am. Chem. Soc., 1964, 86, 3930. [all data]
Potts, Lyus, et al., 1980
Potts, A.W.; Lyus, M.L.; Lee, E.P.F.; Fattahallah, G.H.,
High resolution ultraviolet photoelectron spectra of C6H5X and p-C6H4X2 where X = Cl, Br or I,
J. Chem. Soc. Faraday Trans. 2, 1980, 76, 556. [all data]
Cvitas and Klasinc, 1977
Cvitas, T.; Klasinc, L.,
Photoelectron spectra of bromobenzenes,
Croat. Chem. Acta., 1977, 50, 291. [all data]
Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P.,
Inductive mesomeric effects on the π orbitals of halobenzenes,
Mol. Phys., 1973, 26, 1037. [all data]
Baker, May, et al., 1968
Baker, A.D.; May, D.P.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part VII. The vertical ionisation potentials of benzene and some of its monosubstituted and 1,4-disubstituted derivatives,
J. Chem. Soc. B, 1968, 22. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH(+) ion,0K Enthalpy of formation of positive ion at 0K ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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