Benzene, 1,2-dichloro-
- Formula: C6H4Cl2
- Molecular weight: 147.002
- IUPAC Standard InChIKey: RFFLAFLAYFXFSW-UHFFFAOYSA-N
- CAS Registry Number: 95-50-1
- 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. - Isotopologues:
- Other names: Benzene, o-dichloro-; o-Dichlorobenzene; Cloroben; Dilantin DB; Dowtherm E; 1,2-Dichlorbenzene; 1,2-Dichlorobenzene; Chloroben; o-Dichlorobenzol; Dilatin db; ortho-Dichlorobenzene; o-Dichlorbenzene; o-Dichlorbenzol; Dichlorobenzene, o-; Dizene; DCB; NCI-C54944; ODB; ODCB; Special termite fluid; Termitkil; Chloroden; Dichlorobenzene, ortho; Orthodichlorobenzol; UN 1591; NSC 60644
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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 | 7.89 | kcal/mol | Ccr | Platonov and Simulin, 1984 |
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 |
---|---|---|---|---|---|
ΔfH°liquid | -4.16 ± 0.31 | kcal/mol | Ccb | Sinke and Stull, 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -4.4 ± 0.3 kcal/mol; ALS |
ΔfH°liquid | -3.8 ± 0.4 | kcal/mol | Ccr | Bjellerup and Smith, 1954 | At 293 K; ALS |
ΔfH°liquid | -4.20 ± 0.17 | kcal/mol | Ccb | Hubbard, Knowlton, et al., 1954 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -708. ± 1. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
40.85 | 298.15 | Narbutt, 1918 | T = 197 to 375 K. Cp = 0.27022 + 0.0003024t cal/g*K. Cp value calculated from equation.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 453.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 453.4 | K | N/A | Kailuru and Abburi, 1988 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 453. | K | N/A | Walling and Miller, 1957 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tboil | 453.63 | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.07 K; TRC |
Tboil | 452.65 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.35 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 256.0 ± 0.6 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.2 | kcal/mol | GC | Spieksma, Luijk, et al., 1994 | Based on data from 413. to 453. K.; AC |
ΔvapH° | 11.6 ± 0.02 | kcal/mol | C | An and Zheng, 1989 | AC |
ΔvapH° | 11.9 | kcal/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 360. to 450. K. See also Basarová and Svoboda, 1991.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
451.2 | 1.00 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.0 | 322. | GS | Grayson and Fosbraey, 2006 | Based on data from 301. to 343. K.; AC |
12.2 | 256. | N/A | Rohác, Ruzicka, et al., 1999 | AC |
10.6 | 376. | EB | Rohác, Ruzicka, et al., 1998 | Based on data from 363. to 454. K.; AC |
12.1 | 271. | N/A | Polednicek, Guetachew, et al., 1996 | Based on data from 256. to 287. K.; AC |
12.2 | 258. to 313. | GC | Liu and Dickhut, 1994 | AC |
10.5 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 453. 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 |
---|---|---|---|---|
293.14 to 453.57 | 4.18947 | 1649.55 | -59.836 | McDonald, Shrader, et al., 1959 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.96 | 255.9 | DSC | Wei and Jin, 2009 | See also Wei, 2008.; AC |
3.090 | 256.5 | N/A | Acree, 1991 | AC |
3.0884 | 255.65 | N/A | Narbutt, 1918 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.1 | 255.65 | Narbutt, 1918 | DH |
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
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
C6H3Cl2- + =
By formula: C6H3Cl2- + H+ = C6H4Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 377.1 ± 2.1 | kcal/mol | G+TS | Schlosser, Marzi, et al., 2001 | gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 368.7 ± 2.0 | kcal/mol | IMRE | Schlosser, Marzi, et al., 2001 | gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B |
By formula: C6H4Cl2 = C6H4Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 2.104 | kcal/mol | Eqk | Godnev and Sverdlin, 1961 | gas phase; Correction of 56GOD/SVE; ALS |
Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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) | 9.06 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°(+) ion | 216.1 | kcal/mol | N/A | N/A | |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH(+) ion,0K | 219.1 | kcal/mol | N/A | N/A |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.093668 | ECD | Steelhammer and Wentworth, 1969 | G3MP2B3 calculations indicate an EA of ca. -0.2 eV, unbound.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.06 ± 0.02 | PIPECO | Olesik, Baer, et al., 1986 | LBLHLM |
9.08 ± 0.03 | PE | Ruscic, Klasinc, et al., 1981 | LLK |
9.06 ± 0.02 | PE | Maier and Marthaler, 1978 | LLK |
9.08 ± 0.01 | EQ | Lias and Ausloos, 1978 | LLK |
9.07 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.06 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.24 | PE | Fujisawa, Oonishi, et al., 1991 | Vertical value; LL |
9.23 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
9.08 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H4Cl+ | 12.35 | Cl | EST | Takhistov and Ponomarev, 1994 | LL |
C6H4Cl+ | 12.92 | Cl | EI | Takhistov and Ponomarev, 1994 | Unpublished result of N.S.Khlebnikova, V.M.Orlov, D.A.Ponomarev, and V.V.Takhistov; LL |
De-protonation reactions
C6H3Cl2- + =
By formula: C6H3Cl2- + H+ = C6H4Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 377.1 ± 2.1 | kcal/mol | G+TS | Schlosser, Marzi, et al., 2001 | gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 368.7 ± 2.0 | kcal/mol | IMRE | Schlosser, Marzi, et al., 2001 | gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.
Platonov and Simulin, 1984
Platonov, V.A.; Simulin, Yu.N.,
Experimental determination of the standard enthalpies of formation of polychlorobenzenes. II. Standard enthalpies of formation of dichlorobenzenes,
Russ. J. Phys. Chem. (Engl. Transl.), 1984, 58, 1630-1632. [all data]
Sinke and Stull, 1958
Sinke, G.C.; Stull, D.R.,
Heats of combustion of some organic compounds containing chlorine,
J. Phys. Chem., 1958, 62, 397-401. [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]
Bjellerup and Smith, 1954
Bjellerup, L.; Smith, L.,
Heats of combustion of some organic chloro-compounds,
Kgl. Fysiograph. Sallskap. Lund Forh., 1954, 24, 1-13. [all data]
Hubbard, Knowlton, et al., 1954
Hubbard, W.N.; Knowlton, J.W.; Huffman, H.M.,
Combustion calorimetry of organic chlorine compounds. Heats of combustion of chlorobenzene, the dichlorobenzenes and o- and p-chloroethylbenzene,
J. Phys. Chem., 1954, 58, 396. [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]
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]
Kailuru and Abburi, 1988
Kailuru, R.; Abburi, K.,
Isobaric Vapor-Liquid Equilibria of Methyl Ethyl Ketone(1) + o-Dichlorobenzene(2), + Bromobenzene(2), and + Nitrobenzene(2),
J. Chem. Eng. Data, 1988, 33, 251. [all data]
Walling and Miller, 1957
Walling, C.; Miller, B.,
The Relative Reactivities of Substituted Toluenes toward Chlorine Atoms,
J. Am. Chem. Soc., 1957, 79, 4181. [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, 1943
Lecat, M.,
Azeotropes of Ethyl Urethane and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]
Spieksma, Luijk, et al., 1994
Spieksma, Walter; Luijk, Ronald; Govers, Harrie A.J.,
Determination of the liquid vapour pressure of low-volatility compounds from the Kováts retention index,
Journal of Chromatography A, 1994, 672, 1-2, 141-148, https://doi.org/10.1016/0021-9673(94)80602-0
. [all data]
An and Zheng, 1989
An, Xuwu; Zheng, Xiaolin,
Determination of Standard Enthalpies of Vaporization and Sublimation of Three Dichlorobenzenes,
Acta Phys. Chim. Sin., 1989, 5, 4, 487-491, https://doi.org/10.3866/PKU.WHXB19890421
. [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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Grayson and Fosbraey, 2006
Grayson, B. Terence; Fosbraey, Lynda A.,
Determination of the vapour pressure of pesticides,
Pestic. Sci., 2006, 13, 3, 269-278, https://doi.org/10.1002/ps.2780130308
. [all data]
Rohác, Ruzicka, et al., 1999
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Polednicek, Milos; Aim, Karel; Jose, Jacques; Zábranský, Milan,
Recommended vapour and sublimation pressures and related thermal data for chlorobenzenes,
Fluid Phase Equilibria, 1999, 157, 1, 121-142, https://doi.org/10.1016/S0378-3812(99)00003-5
. [all data]
Rohác, Ruzicka, et al., 1998
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Aim, Karel,
Measurements of Saturated Vapor Pressure above the Liquid Phase for Isomeric Dichlorobenzenes and 1,2,4-Trichlorobenzene,
J. Chem. Eng. Data, 1998, 43, 5, 770-775, https://doi.org/10.1021/je9701442
. [all data]
Polednicek, Guetachew, et al., 1996
Polednicek, M.; Guetachew, T.; Jose, J.; Ruzicka, V.; Rohac, V.; Zabransky, M.,
Vapor pressures and sublimation pressures of dichlorobenzenes (1,2-,1,3-, and 1,4-), trichlorobenzenes (1,2,3- and 1,3,5-), and pentachlorobenzene,
ELDATA: Int. Electron. J. Phys. Chem. Data, 1996, 2, 2, 41. [all data]
Liu and Dickhut, 1994
Liu, Kewen; Dickhut, Rebecca M.,
Saturation vapor pressures and thermodynamic properties of benzene and selected chlorinated benzenes at environmental temperatures,
Chemosphere, 1994, 29, 3, 581-589, https://doi.org/10.1016/0045-6535(94)90445-6
. [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]
McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R.,
Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds.,
J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009
. [all data]
Wei and Jin, 2009
Wei, Dongwei; Jin, Kexin,
(Solid+liquid) equilibria of (naphthalene+isomeric dichlorobenzenes),
The Journal of Chemical Thermodynamics, 2009, 41, 2, 145-149, https://doi.org/10.1016/j.jct.2008.10.005
. [all data]
Wei, 2008
Wei, Dongwei,
(Solid+liquid) equilibria of (phenanthrene+dichlorobenzenes),
Thermochimica Acta, 2008, 479, 1-2, 32-36, https://doi.org/10.1016/j.tca.2008.09.010
. [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]
Schlosser, Marzi, et al., 2001
Schlosser, M.; Marzi, E.; Cottet, F.; Buker, H.H.; Nibbering, N.M.M.,
The acidity of chloro-substituted benzenes: A comparison of gas phase, ab initio, and kinetic data,
Chem. Eur. J., 2001, 7, 16, 3511-3516, https://doi.org/10.1002/1521-3765(20010817)7:16<3511::AID-CHEM3511>3.0.CO;2-U
. [all data]
Godnev and Sverdlin, 1961
Godnev, I.N.; Sverdlin, A.S.,
Equilibrium and dichlorobenzene isomer (Corrections),
Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 231-232. [all data]
Steelhammer and Wentworth, 1969
Steelhammer, J.C.; Wentworth, W.E.,
Correlation of Electron Beam and Thermal Electron Attachment Studies for Some Chloro, Bromo, Iodo Aromatic Compounds,
J. Chem. Phys., 1969, 51, 5, 1802, https://doi.org/10.1063/1.1672262
. [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]
Ruscic, Klasinc, et al., 1981
Ruscic, B.; Klasinc, L.; Wolf, A.; Knop, J.V.,
Photoelectron spectra of and Ab initio calculations on chlorobenzenes. 1. Chlorobenzene and dichlorobenzenes,
J. Phys. Chem., 1981, 85, 1486. [all data]
Maier and Marthaler, 1978
Maier, J.P.; Marthaler, O.,
Emission spectra of the radical cations of 1,3-dichlorobenzene, 1,4-dichlorobenzene and 1,3,5-trichlorobenzene in the gas phase,
Chem. Phys., 1978, 32, 419. [all data]
Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J.,
eIonization energies of organic compounds by equilibrium measurements,
J. Am. Chem. Soc., 1978, 100, 6027. [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]
Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C.,
The effect of fluorine on the electronic spectra and ionization potentials of molecules,
Proc. Roy. Soc. (London), 1960, A258, 459. [all data]
Fujisawa, Oonishi, et al., 1991
Fujisawa, S.; Oonishi, I.; Masuda, S.; Ohno, K.; Harada, Y.,
Penning ionization electron spectroscopy of dichlorobenzenes,
J. Phys. Chem., 1991, 95, 4250. [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]
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]
Takhistov and Ponomarev, 1994
Takhistov, V.V.; Ponomarev, D.A.,
Isodesmic reactions and thermochemistry of ions,
Org. Mass Spectrom., 1994, 29, 395. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH(+) ion,0K Enthalpy of formation of positive ion at 0K ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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