Benzene, chloro-
- Formula: C6H5Cl
- Molecular weight: 112.557
- IUPAC Standard InChIKey: MVPPADPHJFYWMZ-UHFFFAOYSA-N
- CAS Registry Number: 108-90-7
- 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: Chlorobenzene; Monochlorobenzene; MCB; Phenyl Chloride; Benzene chloride; Chlorbenzene; Chlorobenzol; Monochlorbenzene; Chloorbenzeen; Chlorbenzol; Chlorobenzen; Chlorobenzene, mono-; Clorobenzene; Monochloorbenzeen; Monochlorbenzol; Monoclorobenzene; NCI-C54886; Chlorobenzenu; UN 1134; Abluton T30; CP 27; IP Carrier T 40; NSC 8433; Tetrosin SP
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Reaction thermochemistry data
Go To: Top, 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:
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
By formula: Cl- + C6H5Cl = (Cl- C6H5Cl)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 50.21 ± 0.42 | kJ/mol | TDAs | Sieck, 1985 | gas phase; B,M |
![]() | 56.9 ± 4.2 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,B,M |
![]() | 52.7 | kJ/mol | PHPMS | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
![]() | 69.0 | J/mol*K | PHPMS | Sieck, 1985 | gas phase; M |
![]() | 93.7 | J/mol*K | N/A | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 29.7 ± 0.84 | kJ/mol | TDAs | Sieck, 1985 | gas phase; B |
![]() | 29. ± 4.2 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,B,M |
![]() | 27.2 | kJ/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
![]() |
T (K) | Method | Reference | Comment |
---|---|---|---|---|
28. | 300. | PHPMS | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
27. | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
C6H4Cl- + =
By formula: C6H4Cl- + H+ = C6H5Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 1636. ± 7.9 | kJ/mol | Bran | Wenthold and Squires, 1995 | gas phase; B |
![]() | 1633. ± 8.8 | kJ/mol | G+TS | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
![]() | 1633. ± 8.8 | kJ/mol | G+TS | Wenthold, Paulino, et al., 1991 | gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 1602. ± 8.4 | kJ/mol | H-TS | Wenthold and Squires, 1995 | gas phase; B |
![]() | 1598. ± 8.4 | kJ/mol | IMRB | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
![]() | 1598. ± 8.4 | kJ/mol | IMRB | Wenthold, Paulino, et al., 1991 | gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B |
C6H4Cl- + =
By formula: C6H4Cl- + H+ = C6H5Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 1650. ± 5.4 | kJ/mol | Bran | Wenthold and Squires, 1995 | gas phase; B |
![]() | 1631. ± 8.8 | kJ/mol | G+TS | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
![]() | 1631. ± 8.8 | kJ/mol | G+TS | Wenthold, Paulino, et al., 1991 | gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 1618. ± 5.9 | kJ/mol | H-TS | Wenthold and Squires, 1995 | gas phase; B |
![]() | 1598. ± 8.4 | kJ/mol | IMRB | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
![]() | 1598. ± 8.4 | kJ/mol | IMRB | Wenthold, Paulino, et al., 1991 | gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B |
C6H4Cl- + =
By formula: C6H4Cl- + H+ = C6H5Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 1618. ± 8.8 | kJ/mol | G+TS | Andrade and Riveros, 1996 | gas phase; B |
![]() | 1624. ± 8.4 | kJ/mol | Bran | Wenthold and Squires, 1995 | gas phase; B |
![]() | 1622. ± 13. | kJ/mol | G+TS | Wenthold, Paulino, et al., 1991 | gas phase; Between PhF, furan; B |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 1584. ± 8.4 | kJ/mol | IMRE | Andrade and Riveros, 1996 | gas phase; B |
![]() | 1590. ± 8.8 | kJ/mol | H-TS | Wenthold and Squires, 1995 | gas phase; B |
![]() | 1588. ± 13. | kJ/mol | IMRB | Wenthold, Paulino, et al., 1991 | gas phase; Between PhF, furan; B |
![]() | 1586. ± 21. | kJ/mol | IMRB | Bartmess and McIver Jr., 1979 | gas phase; Between H2O, MeOH; B |
By formula: Br- + C6H5Cl = (Br- C6H5Cl)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 46.4 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 11. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B |
Free energy of reaction
![]() |
T (K) | Method | Reference | Comment |
---|---|---|---|---|
11. | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
By formula: C6H7N+ + C6H5Cl = (C6H7N+ C6H5Cl)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 49.0 | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 110. | J/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
![]() |
T (K) | Method | Reference | Comment |
---|---|---|---|---|
17. | 297. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
By formula: C9H12+ + C6H5Cl = (C9H12+ C6H5Cl)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 47.7 | kJ/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 110. | J/mol*K | N/A | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
![]() |
T (K) | Method | Reference | Comment |
---|---|---|---|---|
12. | 300. | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
By formula: NO- + C6H5Cl = (NO- C6H5Cl)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 161. | kJ/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M |
By formula: C6H5Cl + C12H17Cl = C9H11Cl + C9H11Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | -0.84 ± 0.42 | kJ/mol | Eqk | Nesterova, Rozhnov, et al., 1985 | liquid phase; ALS |
By formula: C6H5Cl + C14H21Cl = C10H13Cl + C10H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | -0.25 ± 0.71 | kJ/mol | Eqk | Kovzel, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C9H11Cl + C6H6 = C6H5Cl + C9H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | -0.59 ± 0.42 | kJ/mol | Eqk | Nesterova, Rozhnov, et al., 1985 | liquid phase; ALS |
By formula: C6H5Cl + C14H21Cl = 2C10H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 0. ± 0.1 | kJ/mol | Eqk | Kovzel, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C6H6 + Cl2 = C6H5Cl + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | -134. | kJ/mol | Cm | Kirkbride, 1956 | liquid phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sieck, 1985
Sieck, L.W.,
Thermochemistry of Solvation of NO2- and C6H5NO2- by Polar Molecules in the Vapor Phase. Comparison with Cl- and Variation with Ligand Structure.,
J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049
. [all data]
Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B.,
Gas phase negative ion chemistry of alkylchloroformates,
Can. J. Chem., 1984, 62, 675. [all data]
Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P.,
Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-,
J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014
. [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]
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]
Wenthold and Squires, 1994
Wenthold, P.G.; Squires, R.R.,
Gas-phase properties and reactivity of the acetate radical anion. Determination of the C-H bond strengths in acetic acid and acetate ion,
J. Am. Chem. Soc., 1994, 116, 26, 11890, https://doi.org/10.1021/ja00105a032
. [all data]
Wenthold, Paulino, et al., 1991
Wenthold, P.G.; Paulino, J.A.; Squires, R.R.,
The Absolute Heats of Formation of ortho-Benzyne, meta-Benzyne, and para-Benzyne,
J. Am. Chem. Soc., 1991, 113, 19, 7414, https://doi.org/10.1021/ja00019a044
. [all data]
Andrade and Riveros, 1996
Andrade, P.B.M.; Riveros, J.M.,
Relative Gas-phase Acidities of Fluoro- and Chlorobenzene,
J. Mass Spectrom., 1996, 31, 7, 767, https://doi.org/10.1002/(SICI)1096-9888(199607)31:7<767::AID-JMS345>3.0.CO;2-Q
. [all data]
Bartmess and McIver Jr., 1979
Bartmess, J.E.; McIver Jr.,
The Gas Phase Acidity Scale
in Gas Phase Ion Chemistry, Gas Phase Ion Chemistry, V. 2, M.T. Bowers, Ed., Academic Press, NY, 1979, Ch. 11, Elsevier, 1979. [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]
Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H.,
Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies,
J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034
. [all data]
Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S.,
Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes,
J. Am. Chem. Soc., 1981, 103, 2791. [all data]
Farid and McMahon, 1978
Farid, R.; McMahon, T.B.,
Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0
. [all data]
Nesterova, Rozhnov, et al., 1985
Nesterova, T.N.; Rozhnov, A.M.; Malova, T.N.; Kovzel, E.N.,
Molar enthalpies of formation of isopropylchlorobenzenes derived from equilibrium measurements,
J. Chem. Thermodyn., 1985, 17, 649-656. [all data]
Kovzel, Nesterova, et al., 1981
Kovzel, E.N.; Nesterova, T.N.; Rozhnov, A.M.; Kartavtseva, T.A.,
Study of equilibrium in in the chlorobenzene-butylchlorobenzenes systems,
Termodin. Organ. Soedin., 1981, 65-68. [all data]
Kirkbride, 1956
Kirkbride, F.W.,
The heats of chlorination of some hydrocarbons and their chloro-derivatives,
J. Appl. Chem., 1956, 6, 11-21. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature rG°
Free energy of reaction at standard conditions rH°
Enthalpy of reaction at standard conditions rS°
Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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