Benzene, chloro-

• Formula: C₆H₅Cl
• Molecular weight: 112.557
• IUPAC Standard InChI: InChI=1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H Copy

  
• IUPAC Standard InChIKey: MVPPADPHJFYWMZ-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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

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

Constant pressure heat capacity of liquid

Constant pressure heat capacity of solid

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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

 +  = ( • )

By formula: Cl^- + C₆H₅Cl = (Cl^- • C₆H₅Cl)

Free energy of reaction

C₆H₄Cl^- +  =

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

C₆H₄Cl^- +  =

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

C₆H₄Cl^- +  =

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

 +  = ( • )

By formula: Br^- + C₆H₅Cl = (Br^- • C₆H₅Cl)

Free energy of reaction

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₅Cl = (C₆H₇N⁺ • C₆H₅Cl)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₆H₅Cl = (C₉H₁₂⁺ • C₆H₅Cl)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

 +  = ( • )

By formula: NO^- + C₆H₅Cl = (NO^- • C₆H₅Cl)

 +  =  + 

By formula: C₆H₅Cl + C₁₂H₁₇Cl = C₉H₁₁Cl + C₉H₁₁Cl

 +  =  + 

By formula: C₆H₅Cl + C₁₄H₂₁Cl = C₁₀H₁₃Cl + C₁₀H₁₃Cl

 +  =  + 

By formula: C₉H₁₁Cl + C₆H₆ = C₆H₅Cl + C₉H₁₂

 +  = 2

By formula: C₆H₅Cl + C₁₄H₂₁Cl = 2C₁₀H₁₃Cl

 +  =  + 

By formula: C₆H₆ + Cl₂ = C₆H₅Cl + HCl

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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₆H₅Cl⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₄Cl^- +  =

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

C₆H₄Cl^- +  =

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

C₆H₄Cl^- +  =

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

Ion clustering 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Br^- + C₆H₅Cl = (Br^- • C₆H₅Cl)

Free energy of reaction

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₅Cl = (C₆H₇N⁺ • C₆H₅Cl)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₆H₅Cl = (C₉H₁₂⁺ • C₆H₅Cl)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

 +  = ( • )

By formula: Cl^- + C₆H₅Cl = (Cl^- • C₆H₅Cl)

Free energy of reaction

 +  = ( • )

By formula: NO^- + C₆H₅Cl = (NO^- • C₆H₅Cl)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (10 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution
• SOLUTION (10% CCl4 FOR 3800-1250, 10% CS2 FOR 1250-450 CM^-1) VS SOLVENT; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

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

• gas

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

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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For Zoom

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Platonov and Simulin, 1985
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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]

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Momigny, J.; Goffart, C.; D'Or, L., Photoionization studies by total ionization measurements. I. Benzene and its monohalogeno derivatives, Intern. J. Mass Spectrom. Ion Phys., 1968, 1, 53. [all data]

Quemerais, Morlais, et al., 1967
Quemerais, A.; Morlais, M.; Robin, S., Spectres d'absorption du benzene et du monochlorobenzene dans l'ultraviolet de 1300 a 2300 A, Compt. Rend., 1967, 265, 649. [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]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [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]

Sell and Kupperman, 1978
Sell, J.A.; Kupperman, A., Angular distributions in the photoelectron spectra of benzene and its monohalogenated derivatives, Chem. Phys., 1978, 33, 367. [all data]

Klasinc, Novak, et al., 1978
Klasinc, L.; Novak, I.; Scholz, M.; Kluge, G., Photoelektronenspektren substituierter Pyridine und Benzole und ihre Interpretation durch die CNDO/SWW-Methode, Croat. Chem. Acta, 1978, 51, 43. [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]

Momigny, 1959
Momigny, J., Determination et discussion des potentials d'apparition d'ions fragmentaires dans le benzene et ses derives monohalogenes, Bull. Soc. Roy. Sci. Liege, 1959, 28, 251. [all data]

Ripoche, Dimicoli, et al., 1991
Ripoche, X.; Dimicoli, I.; Botter, R., Unimolecular decay rates for laser induced Cl loss from energy selected chlorobenzene cations [E_o(C₆H₅Cl⁺ Ü C₆H₅⁺ + Cl)=2.74±0.02 eV; cited data derived using recommended IP for chlorobenzene.], Int. J. Mass Spectrom. Ion Processes, 1991, 107, 165. [all data]

Burgers and Holmes, 1984
Burgers, P.C.; Holmes, J.L., Fragmentation rate constants and appearance energies for reactions having a large kinetic shift and the energy partitioning in their metastable decomposition, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 15. [all data]

Rosenstock, Stockbauer, et al., 1980
Rosenstock, H.M.; Stockbauer, R.; Parr, A.C., Photoelectron-photoion coincidence study of the bromobenzene ion, J. Chem. Phys., 1980, 73, 773. [all data]

Rosenstock, Stockbauer, et al., 1979
Rosenstock, H.M.; Stockbauer, R.; Parr, A.C., Kinetic shift in chlorobenzene ion fragmentation and the heat of formation of the phenyl ion, J. Chem. Phys., 1979, 71, 3708. [all data]

Johnstone and Mellon, 1972
Johnstone, R.A.W.; Mellon, F.A., Electron-impact ionization and appearance potentials, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1209. [all data]

Majer and Patrick, 1962
Majer, J.R.; Patrick, C.R., Electron impact on some halogenated aromatic compounds, J. Chem. Soc. Faraday Trans., 1962, 58, 17. [all data]

Grammaticakis, 1949
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'ultraviolet moyen des anilines orthosubstituees. II. Ortho-halogenanilines N-substituees, Bull. Soc. Chim. Fr., 1949, 16, 761. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  Cp,solid	Constant pressure heat capacity of solid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  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
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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