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Benzene, 1-chloro-4-nitro-

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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

Quantity Value Units Method Reference Comment
Deltafsolid-48.74kJ/molCcbMasalitinova, Oleinikova, et al., 1981ALS
Quantity Value Units Method Reference Comment
Deltacsolid-2907.5 ± 3.2kJ/molCcbMasalitinova, Oleinikova, et al., 1981ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
250.2298.Marchidan and Ciopec, 1978T = 298 to 467 K.; DH

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
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
Tboil515.2KN/AWeast and Grasselli, 1989BS
Tboil512.25KN/ALecat, 1947Uncertainty assigned by TRC = 0.6 K; TRC
Tboil512.25KN/ALecat, 1943Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus356. ± 2.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Deltasub74.7 ± 0.1kJ/molGSVerevkin and Schick, 2003Based on data from 303. - 339. K.; AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
386.20.01Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
51.3400.AStephenson and Malanowski, 1987Based on data from 385. - 515. K.; AC
36.900518.N/AVorob'ev, Borisov, et al., 1981DH

Entropy of vaporization

DeltavapS (J/mol*K) Temperature (K) Reference Comment
71.2518.Vorob'ev, Borisov, et al., 1981DH

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
83.2293.MEStephenson and Malanowski, 1987Based on data from 283. - 303. K. See also Swan and Mack, 1925.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
15.03355.1N/AStraka, Ruzicka, et al., 2007AC
16.17356.1DSCVerevkin and Schick, 2003AC
11.85354.6N/ADomalski and Hearing, 1996AC
14.1357.N/AMasalitinova, Oleinikova, et al., 1981, 2AC
18.030358.N/AVorob'ev, Borisov, et al., 1981DH
11.850354.6N/AMarchidan and Ciopec, 1978DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
69.9358.Vorob'ev, Borisov, et al., 1981DH
33.4354.6Marchidan and Ciopec, 1978DH

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 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. 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

Bromine anion + Benzene, 1-chloro-4-nitro- = (Bromine anion bullet Benzene, 1-chloro-4-nitro-)

By formula: Br- + C6H4ClNO2 = (Br- bullet C6H4ClNO2)

Quantity Value Units Method Reference Comment
Deltar67.4 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar92.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar28. ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
28.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

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 as indicated in comments:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Electron affinity determinations

EA (eV) Method Reference Comment
1.26 ± 0.10TDEqChowdhury, Heinis, et al., 1986«DELTA»Gea(423 K) = -28.2 kcal/mol; «DELTA»Sea = -2.0 eu.; B
1.232 ± 0.087IMREHuh, Kang, et al., 1999«DELTA»G(EA) 343K; anchored to «DELTA»G value. Including anchor «DELTA»S, EA is ca. 0.4 kcal/mol more bound.; B
<1.270 ± 0.050PDMock and Grimsrud, 1989B
1.232 ± 0.048IMREFukuda and McIver, 1985«DELTA»Gea(355 K) = -27.7 kcal/mol; «DELTA»Sea =-2.0, est. from data in Chowdhury, Heinis, et al., 1986; B

Ionization energy determinations

IE (eV) Method Reference Comment
10. ± 0.1EIBrown, 1970RDSH
9.99PEBaker, May, et al., 1968Vertical value; RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H4Cl+12.3 ± 0.1NO2EIBrown, 1970RDSH
C6H4OCl+10.6 ± 0.1NOEIBrown, 1970RDSH

Ion clustering data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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:
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

Bromine anion + Benzene, 1-chloro-4-nitro- = (Bromine anion bullet Benzene, 1-chloro-4-nitro-)

By formula: Br- + C6H4ClNO2 = (Br- bullet C6H4ClNO2)

Quantity Value Units Method Reference Comment
Deltar67.4 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar92.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar28. ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
28.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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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Mass spectrum
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Additional Data

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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-1367
NIST MS number 229516

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.


Gas Chromatography

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryUltra-11189.Okumura, 199125. m/0.32 mm/0.25 «mu»m, 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
CapillarySPB-11187.Vezzani, Moretti, et al., 1994Column length: 30. m; Column diameter: 0.32 mm; Program: not specified
CapillaryOV-11193.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySuperox 0.6; Carbowax 20M1887.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
CapillaryCarbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.1887.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
CapillarySuperox 0.6; Carbowax 20M1902.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

Lee's RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP5-MS212.Vrana, Paschke, et al., 200530. m/0.25 mm/0.25 «mu»m, Helium, 50. C @ 5. min, 5. K/min, 280. C @ 10. min

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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.

Masalitinova, Oleinikova, et al., 1981
Masalitinova, T.N.; Oleinikova, T.P.; Ryadnenko, V.L.; Kiseleva, N.N.; Lebedeva, N.D., Thermal effects of the hydrogenation of chloronitrobenzenes, J. Appl. Chem. USSR, 1981, 54, 1551-1554, In original 1799. [all data]

Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M., Relative enthalpies and related thermodynamic functions of some organic compounds by drop calorimetry, J. Therm. Anal., 1978, 14, 131-150. [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]

Lecat, 1947
Lecat, M., Some azeotropes of which one constituant is heterocyclic nitrogen, Ann. Soc. Sci. Bruxelles, Ser. 1, 1947, 61, 73. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Verevkin and Schick, 2003
Verevkin, Sergey P.; Schick, Christoph, Determination of vapor pressures, enthalpies of sublimation, enthalpies of vaporization, and enthalpies of fusion of a series of chloro-aminobenzenes and chloro-nitrobenzenes, Fluid Phase Equilibria, 2003, 211, 2, 161-177, https://doi.org/10.1016/S0378-3812(03)00181-X . [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]

Vorob'ev, Borisov, et al., 1981
Vorob'ev, G.I.; Borisov, N.N.; Novikova, G.A.; Efimova, V.L., Physicochemical properties of 2,4-dichloro-1-(4-nitrophenoxy)benzene, Khim. Prom. (Moscow), 1981, (12), 728. [all data]

Swan and Mack, 1925
Swan, Thomas H.; Mack, Edward, VAPOR PRESSURES OF ORGANIC CRYSTALS BY AN EFFUSION METHOD, J. Am. Chem. Soc., 1925, 47, 8, 2112-2116, https://doi.org/10.1021/ja01685a005 . [all data]

Straka, Ruzicka, et al., 2007
Straka, Martin; Ruzicka, Kvetoslav; Ruzicka, Vlastimil, Heat Capacities of Chloroanilines and Chloronitrobenzenes, J. Chem. Eng. Data, 2007, 52, 4, 1375-1380, https://doi.org/10.1021/je700080k . [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]

Masalitinova, Oleinikova, et al., 1981, 2
Masalitinova, T.N.; Oleinikova, T.P.; Ryadnenko, V.L.; Kiseleva, N.N.; Lebedeva, N.D., Zh. Prikl. Khim. (Leningrad), 1981, 54, 1799. [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]

Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A- + B = A + B-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Mock and Grimsrud, 1989
Mock, R.S.; Grimsrud, E.P., Gas-Phase Electron Photodetachment Spectroscopy of the Molecular Anions of Nitroaromatic Hydrocarbons at Atmospheric Pressure, J. Am. Chem. Soc., 1989, 111, 8, 2861, https://doi.org/10.1021/ja00190a020 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry. IX. Competing [M-NO2] and [M-NO] reactions in substituted nitrobenzenes. Approximate activation energies from ionization and appearance potentials, Org. Mass Spectrom., 1970, 4, 533. [all data]

Baker, May, et al., 1968
Baker, A.D.; May, D.P.; Turner, D.W., Molecular photoelectron spectroscopy. Part VII. The vertical ionisation potentials of benzene and some of its monosubstituted and 1,4-disubstituted derivatives, J. Chem. Soc. B, 1968, 22. [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]

Vezzani, Moretti, et al., 1994
Vezzani, S.; Moretti, P.; Castello, G., Fast and Accurate Method for the Automatic Prediction of Programmed-Temperature Retention Times, J. Chromatogr. A, 1994, 677, 2, 331-343, https://doi.org/10.1016/0021-9673(94)80161-4 . [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]

Vrana, Paschke, et al., 2005
Vrana, B.; Paschke, H.; Paschke, A.; Popp, P.; Schuurmann, G., Performance of semipermeable membrane devices for sampling of organic contaminants in groun water, J. Envirom. Monit., 2005, 7, 5, 500-508, https://doi.org/10.1039/b411645c . [all data]


Notes

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