1,1'-Biphenyl, 4-chloro-
- Formula: C12H9Cl
- Molecular weight: 188.653
- IUPAC Standard InChIKey: FPWNLURCHDRMHC-UHFFFAOYSA-N
- CAS Registry Number: 2051-62-9
- 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: Biphenyl, 4-chloro-; p-Chlorobiphenyl; 4-Chloro-1,1'-biphenyl; 4-Chlorobiphenyl; 4-Chlorodiphenyl; p-Chlorodiphenyl; 1-Chloro-4-phenylbenzene; PCB 3
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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 |
---|---|---|---|---|---|
ΔcH°solid | -6040.06 | kJ/mol | Ccb | Brull, 1935 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 256.9 | J/mol*K | N/A | Geidarov, Dzhafarov, et al., 1975 | DH |
S°solid,1 bar | 256.90 | J/mol*K | N/A | Geidarov, Karasharli, et al., 1977 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
243.76 | 298.15 | Geidarov, Karasharli, et al., 1977 | Based on previously published work of authors, not available in detail, on Cp 12 to 370 K.; DH |
243.8 | 298.15 | Geidarov, Dzhafarov, et al., 1975 | T = 12 to 370 K.; DH |
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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 564.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 555. | K | N/A | Frinton Laboratories Inc., 1986 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 348.55 | K | N/A | Geidarov, Karasharli, et al., 1977, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 348.55 | K | N/A | Geidarov, Dzhafarov, et al., 1975, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 347.9 | K | N/A | Geidarov, Dzhafarov, et al., 1974 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 71.6 ± 0.7 | kJ/mol | CGC | Puri, Chickos, et al., 2001 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
66.8 | 368. | GC | Falconer and Bidleman, 1994 | Based on data from 343. to 393. K.; AC |
65.9 | 466. | A | Stephenson and Malanowski, 1987 | Based on data from 451. to 536. K.; AC |
59.0 | 384. | A | Stephenson and Malanowski, 1987 | Based on data from 369. to 566. K. See also Stull, 1947.; AC |
67.8 | 378. | TE | Ferro, Piacente, et al., 1983 | Based on data from 348. to 409. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369.6 to 566.1 | 5.07749 | 2752.545 | -23.404 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
86.0 ± 0.9 | 278. | GS | Wania, Shiu, et al., 1994 | Based on data from 253. to 303. K.; AC |
73.7 ± 0.7 | 326. | TE,ME | Ferro, Piacente, et al., 1983 | Based on data from 306. to 346. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.318 | 348.55 | Geidarov, Dzhafarov, et al., 1975 | DH |
13.318 | 348.55 | Geidarov, Karasharli, et al., 1977 | DH |
13.32 | 348.6 | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.21 | 348.55 | Geidarov, Dzhafarov, et al., 1975 | DH |
38.21 | 348.55 | Geidarov, Karasharli, et al., 1977 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference |
---|---|---|
8.10 ± 0.02 | PE | Maier and Turner, 1972 |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
- SOLUTION (10% IN CCl4 FOR 3800-1340 AND 10% IN CS2 FOR 1340-450 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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
View image of digitized spectrum (can be printed in landscape orientation).
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 | NIST Mass Spectrometry Data Center, 1994 |
NIST MS number | 133301 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-101 | 200. | 1586. | Albro, Haseman, et al., 1977 | Chromosorb W HP (80-100 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1542. | Kozloski, 1985 | He, 5. K/min; Column length: 10. m; Column diameter: 0.21 mm; Tstart: 60. C; Tend: 210. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 1564. | Zenkevich, Moeder, et al., 2004 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 3. min, 3. K/min, 280. C @ 20. min |
Capillary | SPB-1 | 1548. | Nakano, Tsuji, et al., 1987 | 30. m/0.25 mm/0.25 μm, 4. K/min; Tstart: 130. C; Tend: 280. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 1549. | Zenkevich and Chupalov, 1996 | Program: not specified |
Capillary | Apolane | 1564. | Bush, Murphy, et al., 1985 | He; Column length: 50. m; Column diameter: 0.25 mm; Program: 70 0C (2 min) 10 0C/min (6 min) 2 0C/min -> 250 0C |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Brull, 1935
Brull, L.,
Sui calori di combustione di alcuni derivati del bifenil,
Gazz. Chim. Ital., 1935, 65, 19-28. [all data]
Geidarov, Dzhafarov, et al., 1975
Geidarov, Kh.I.; Dzhafarov, O.I.; Karasharli, K.A.; Kostryukov, V.N.,
True heat capacity of p-chlorobiphenyl at 12 to 370 K,
Zhur. Fiz. Khim., 1975, 49, 493-494. [all data]
Geidarov, Karasharli, et al., 1977
Geidarov, Kh.I.; Karasharli, K.A.; Dzhafarov, O.I.,
Analysis of the results of the thermodynamic investigation of diphenyl derivatives,
Azerb. Khim. Zhur., 1977, (5), 112-115. [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]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]
Geidarov, Karasharli, et al., 1977, 2
Geidarov, K.I.; Karasharli, K.A.; Dzhafarov, O.I.,
Analysis of the results of the thermodynamic investigation of diphenyl devivatives,
Azerb. Khim. Zh., 1977, 1977, 112-5. [all data]
Geidarov, Dzhafarov, et al., 1975, 2
Geidarov, K.I.; Dzhafarov, O.I.; Karasharli, K.A.; Kostryukov, V.N.,
True heat capacity of p-chlorobiphenyl at 12 to 370 K,
Zh. Fiz. Khim., 1975, 49, 493-4. [all data]
Geidarov, Dzhafarov, et al., 1974
Geidarov, K.I.; Dzhafarov, O.I.; Karasharli, K.A.; Kostryukov, V.N.,
The heat capacity of 2-chlorobiphenyl in the range 12 - 327 k,
Zh. Fiz. Khim., 1974, 48, 1147-9. [all data]
Puri, Chickos, et al., 2001
Puri, Swati; Chickos, James S.; Welsh, William J.,
Determination of Vaporization Enthalpies of Polychlorinated Biphenyls by Correlation Gas Chromatography,
Anal. Chem., 2001, 73, 7, 1480-1484, https://doi.org/10.1021/ac001246p
. [all data]
Falconer and Bidleman, 1994
Falconer, Renee L.; Bidleman, Terry F.,
Vapor pressures and predicted particle/gas distributions of polychlorinated biphenyl congeners as functions of temperature and ortho-chlorine substitution,
Atmospheric Environment, 1994, 28, 3, 547-554, https://doi.org/10.1016/1352-2310(94)90130-9
. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Ferro, Piacente, et al., 1983
Ferro, Daniela; Piacente, Vincenzo; Scardala, Paolo,
Torsion---Knudsen effusion vapour-pressure measurement of o, m and p-chlorobiphenyls,
Thermochimica Acta, 1983, 68, 2-3, 329-339, https://doi.org/10.1016/0040-6031(83)80235-4
. [all data]
Wania, Shiu, et al., 1994
Wania, Frank; Shiu, Wan-Ying; Mackay, Donald,
Measurement of the Vapor Pressure of Several Low-Volatility Organochlorine Chemicals at Low Temperatures with a Gas Saturation Method,
J. Chem. Eng. Data, 1994, 39, 3, 572-577, https://doi.org/10.1021/je00015a039
. [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]
Maier and Turner, 1972
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls,
Faraday Discuss. Chem. Soc., 1972, 54, 149. [all data]
Albro, Haseman, et al., 1977
Albro, P.W.; Haseman, J.K.; Clemmer, T.A.; Corbett, B.J.,
Identification of the Individual Polychlorinated Biphenyls in a Mixture by Gas-Liquid Chromatography,
J. Chromatogr., 1977, 136, 1, 147-153, https://doi.org/10.1016/S0021-9673(00)83003-4
. [all data]
Kozloski, 1985
Kozloski, R.P.,
Polychlorinated biphenyl retention time standards obtained by chemical dechlorination of polychlorinated biphenyl isomers,
J. Chromatogr., 1985, 318, 211-219, https://doi.org/10.1016/S0021-9673(01)90682-X
. [all data]
Zenkevich, Moeder, et al., 2004
Zenkevich, I.G.; Moeder, M.; Koeller, G.; Schrader, S.,
Using new structurally related additive schemes in the precalculation of gas chromatographic retention indices of polychlorinated hydroxybiphenyls on HP-5 stationary phase,
J. Chromatogr. A, 2004, 1025, 2, 227-236, https://doi.org/10.1016/j.chroma.2003.10.106
. [all data]
Nakano, Tsuji, et al., 1987
Nakano, T.; Tsuji, M.; Okuno, T.,
Analytical methods for PCB using GC/ECD and GC/MS with capillary column,
Report of the Environmental Science Institute of Hyoho Prefecture, 1987, 19, 57-62. [all data]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]
Bush, Murphy, et al., 1985
Bush, B.; Murphy, M.J.; Connor, S.; Snow, J.; Barnard, E.,
Improvements in Glass Capillary Gas Chromatographic Polychlorobiphenyl Analysis,
J. Chromatogr. Sci., 1985, 23, 11, 509-515, https://doi.org/10.1093/chromsci/23.11.509
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Ttriple Triple point temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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