Phenol, 3,5-dichloro-

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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
Δfgas-148.2 ± 1.5kJ/molCcrRibeiro Da Silva, Ferrao, et al., 1994HCl (1:600 H2O)

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

Quantity Value Units Method Reference Comment
Δfsolid-231.0 ± 1.0kJ/molCcrRibeiro Da Silva, Ferrao, et al., 1994HCl (1:600 H2O)
Quantity Value Units Method Reference Comment
Δcsolid-2749.1 ± 0.6kJ/molCcrRibeiro Da Silva, Ferrao, et al., 1994HCl (1:600 H2O)

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil506.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus341.0KN/APoeti, Faneli, et al., 1982Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δsub82.8 ± 1.1kJ/molCRibeiro Da Silva, Ferrao, et al., 1994HCl (1:600 H2O); ALS
Δsub82.8 ± 1.1kJ/molCda Silva, 1994AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
396.20.01Weast and Grasselli, 1989BS

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Reference Comment
71.8284.Stephenson and Malanowski, 1987Based on data from 273. - 295. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
20.509341.0Poeti, Fanelli, et al., 1982DH
20.51341.Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
60.14341.0Poeti, Fanelli, et al., 1982DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 by: John E. Bartmess

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

C6H3Cl2O- + Hydrogen cation = Phenol, 3,5-dichloro-

By formula: C6H3Cl2O- + H+ = C6H4Cl2O

Quantity Value Units Method Reference Comment
Δr1399. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1370. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

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 compiled by: John E. Bartmess

View reactions leading to C6H4Cl2O+ (ion structure unspecified)

De-protonation reactions

C6H3Cl2O- + Hydrogen cation = Phenol, 3,5-dichloro-

By formula: C6H3Cl2O- + H+ = C6H4Cl2O

Quantity Value Units Method Reference Comment
Δr1399. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1370. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

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 Japan AIST/NIMC Database- Spectrum MS-NW-1278
NIST MS number 233457

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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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UVVis spectrum
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Additional Data

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Source Goldschmidt and Suchanek, 1957
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 1125
Instrument n.i.g.
Melting point 68
Boiling point 233

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySE-30160.1375.Evans and Haken, 1989Column length: 25. m; Column diameter: 0.32 mm
CapillarySE-30140.1358.Korhonen, 1984 
CapillarySE-30160.1375.Korhonen, 1984 
CapillarySE-30180.1392.Korhonen, 1984 

Kovats' RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
PackedSE-301391.Grzybowski, Lamparczyk, et al., 1980Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryFFAP160.2675.Evans and Haken, 1989Column length: 25. m; Column diameter: 0.35 mm
CapillaryFFAP160.2675.Korhonen, 1984 
CapillaryFFAP180.2691.Korhonen, 1984 
CapillaryFFAP200.2713.Korhonen, 1984 

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillarySE-301367.Korhonen, 198410. K/min; Tstart: 100. C
CapillarySE-301362.Korhonen, 19842. K/min; Tstart: 100. C
CapillarySE-301362.Korhonen, 19846. K/min; Tstart: 100. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1399.9Tret'yakov, 200730. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryFFAP2707.Korhonen, 198410. K/min; Tstart: 100. C
CapillaryFFAP2670.Korhonen, 19842. K/min; Tstart: 100. C
CapillaryFFAP2700.Korhonen, 19846. K/min; Tstart: 100. C

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryUltra-11370.Okumura, 199125. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPTE-51400.Nakano, Fujimori, et al., 199225. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min)
CapillaryUltra-21395.Nakano, Fujimori, et al., 199225. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min)
CapillarySE-301391.Peterson, 1992Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.1391.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

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

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

Ribeiro Da Silva, Ferrao, et al., 1994
Ribeiro Da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Jiye, F., Standard enthalpies of combustion of the six dichlorophenols by rotating-bomb calorimetry, J. Chem. Thermodyn., 1994, 26, 839-846. [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]

Poeti, Faneli, et al., 1982
Poeti, G.; Faneli, E.; Braghetti, M.J., A differential scanning calorimetric study of some phenol derivatives, Therm. Anal., 1982, 24, 2, 273, https://doi.org/10.1007/BF01913681 . [all data]

da Silva, 1994
da Silva, M., Standard enthalpies of combustion of the six dichlorophenols by rotating-bomb calorimetry, The Journal of Chemical Thermodynamics, 1994, 26, 8, 839-846, https://doi.org/10.1006/jcht.1994.1100 . [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]

Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M., A differential scanning calorimetric study of some phenol derivatives, J. Therm. Anal., 1982, 24(2), 273-279. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Goldschmidt and Suchanek, 1957
Goldschmidt, s.; Suchanek, L., Versuche zur darstellung 2.6.2'.6'-tetra-substituierter diphenochinone, Chem. Ber., 1957, 90, 19-28. [all data]

Evans and Haken, 1989
Evans, M.B.; Haken, J.K., Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds, J. Chromatogr., 1989, 468, 373-382, https://doi.org/10.1016/S0021-9673(00)96332-5 . [all data]

Korhonen, 1984
Korhonen, I.O.O., Gas-liquid chromatographic analyses. XXXI. Retention increments of isomeric chlorophenols on low-polarity (SE-30) and polar (FFAP) capillary columns, J. Chromatogr., 1984, 315, 185-200, https://doi.org/10.1016/S0021-9673(01)90736-8 . [all data]

Grzybowski, Lamparczyk, et al., 1980
Grzybowski, J.; Lamparczyk, H.; Nasal, A.; Radecki, A., Relationship between the retention indices of phenols on polar and non-polar stationary phases, J. Chromatogr., 1980, 196, 2, 217-223, https://doi.org/10.1016/S0021-9673(00)80441-0 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Nakano, Fujimori, et al., 1992
Nakano, T.; Fujimori, K.; Takaishi, Y.; Okuno, T., GC/MS-SIM analysis of polychlorobenzenes, polychlorophenols and polychloronaphthalenes, Report of the Environmental Science Institute of Hyogo Prefecture, 1992, 24, 30-37. [all data]

Peterson, 1992
Peterson, K.L., Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols, Anal. Chem., 1992, 64, 4, 379-386, https://doi.org/10.1021/ac00028a011 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [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, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References