Benzene, 1,4-dichloro-

• Formula: C₆H₄Cl₂
• Molecular weight: 147.002
• IUPAC Standard InChI: InChI=1S/C6H4Cl2/c7-5-1-2-6(8)4-3-5/h1-4H Copy

  
• IUPAC Standard InChIKey: OCJBOOLMMGQPQU-UHFFFAOYSA-N Copy
• CAS Registry Number: 106-46-7
• 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.
• Isotopologues:
  • 1,4-Dichlorobenzene-D4
• Other names: Benzene, p-dichloro-; p-Chlorophenyl chloride; p-Dichlorobenzene; Di-chloricide; Evola; Paradi; Paradow; Paramoth; Persia-Perazol; PDB; Santochlor; 1,4-Dichlorobenzene; p-Dichlorobenzol; Paradichlorobenzol; para-Dichlorobenzene; p-Dichloorbenzeen; p-Dichlorbenzol; p-Diclorobenzene; Dichlorobenzene; Dichlorobenzene, p-; NCI-C54955; para crystals; Paracide; Paranuggets; Parazene; 1,4-Dichloorbenzeen; 1,4-Dichlor-benzol; 1,4-Diclorobenzene; Dichlorobenzene, para; Globol; Paradichlorbenzol; Rcra waste number U070; Rcra waste number U071; Rcra waste number U072; UN 1592; Dichlorocide; Kaydox; p-Dichlorbenzene; NSC 36935; 1,4-chlorobenzene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry 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:
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

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₃Cl₂^- +  =

By formula: C₆H₃Cl₂^- + H⁺ = C₆H₄Cl₂

Mass spectrum (electron ionization)

Go To: Top, Gas phase 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry 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.

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]

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]

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]

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]

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]

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]

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]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry-IV. The [M - Cl] reaction in substituted chlorobenzenes and the question of molecular ion isomerization, Org. Mass Spectrom., 1970, 3, 639. [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]

Notes

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  ΔfH(+) ion,0K	Enthalpy of formation of positive ion at 0K
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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