Phenol, 4-nitro-

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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-114.7 ± 1.2kJ/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Δfgas-117.7 ± 2.0kJ/molCcbFinch, Gardner, et al., 1983 

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
Δfsolid-207.1 ± 1.1kJ/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δfsolid-212.4 ± 1.0kJ/molCcbFinch, Gardner, et al., 1983ALS
Δfsolid-226.7kJ/molCcbRinkenbach, 1930Author hf298_condensed[kcal/mol]=-56.50; ALS
Δfsolid-209.kJ/molCcbSwarts, 1914See 14SWA2; ALS
Quantity Value Units Method Reference Comment
Δcsolid-2868.5 ± 1.0kJ/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δcsolid-2863.21 ± 0.54kJ/molCcbFinch, Gardner, et al., 1983ALS
Δcsolid-2848.9kJ/molCcbRinkenbach, 1930Author hf298_condensed[kcal/mol]=-56.50; ALS
Δcsolid-2874.kJ/molCcbGarner and Abernethy, 1921ALS
Δcsolid-2879.6kJ/molCcbSwarts, 1914See 14SWA2; ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
144.283.Campbell and Campbell, 1941T = 273 to 293 K. Value given as Cp = 0.248 cal/g over temperature range 0 to 20°C.; 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
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
Tboil552.2KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus385. ± 10.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Δsub92.39 ± 0.43kJ/molCSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δsub92.4kJ/molCSabbah and Gouali, 1994, 2AC
Δsub99. ± 1.kJ/molMEParsons, Rochester, et al., 1971Based on data from 305. - 352. K.; AC

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
91. ± 2.343.VWolf and Weghofer, 1938ALS
91.2 ± 1.7339. - 351.N/ATrieschmann, 1935See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
30.118385.15Singh and Kumar, 1986DH
18.254387.0Poeti, Fanelli, et al., 1982DH
11.0386.4Musuc, Razus, et al., 2002AC
18.25388.2Domalski and Hearing, 1996See also Sabbah and Gouali, 1994, 2.; AC
19.300368.75Booss and Hauschildt, 1972DH
24.271387.Campbell and Campbell, 1941DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
78.2385.15Singh and Kumar, 1986DH
47.17387.0Poeti, Fanelli, et al., 1982DH
52.3368.75Booss and Hauschildt, 1972DH
62.7387.Campbell and Campbell, 1941DH

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 + Phenol, 4-nitro- = (Bromine anion • Phenol, 4-nitro-)

By formula: Br- + C6H5NO3 = (Br- • C6H5NO3)

Quantity Value Units Method Reference Comment
Δr119. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr78.2 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
78.2423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

C6H4NO3- + Hydrogen cation = Phenol, 4-nitro-

By formula: C6H4NO3- + H+ = C6H5NO3

Quantity Value Units Method Reference Comment
Δr1371. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1343. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
980.6000.XN/A 
2.6×10+69100.MN/AIt is assumed here that the thermodynamic data in missing citation refers to the units [mol/dm3] and [atm] as standard states.

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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H5NO3+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.1PEKobayashi and Nagakura, 1975LLK
7.38EIJohnstone and Mellon, 1973LLK
8.8 ± 0.1EIBrown, 1970RDSH
9.52EICrable and Kearns, 1962RDSH
9.38PEKobayashi and Nagakura, 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5O+11.9 ± 0.1NO2EIBrown, 1970RDSH
C6H5O2+9.9 ± 0.1NOEIBrown, 1970RDSH

De-protonation reactions

C6H4NO3- + Hydrogen cation = Phenol, 4-nitro-

By formula: C6H4NO3- + H+ = C6H5NO3

Quantity Value Units Method Reference Comment
Δr1371. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1343. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

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

Bromine anion + Phenol, 4-nitro- = (Bromine anion • Phenol, 4-nitro-)

By formula: Br- + C6H5NO3 = (Br- • C6H5NO3)

Quantity Value Units Method Reference Comment
Δr119. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr78.2 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
78.2423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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-1737
NIST MS number 229414

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 Grammaticakis, 1951
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. 99
Instrument n.i.g.
Melting point 113.8

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-1190.1530.Erdmann, Rochholz, et al., 1992Large deviations from similar measurements
PackedE-301150.1588.Verevkin, Belen'kaya, et al., 1990He; Column length: 1.0 m
PackedSE-30204.1562.Mitchell and Vernon, 1972 

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

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-51544.8Van Durme, Dewulf, et al., 2007Program: not specified

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

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-1011527.2Ferchichi and Messadi, 19944. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 30. C; Tend: 250. C
CapillaryDB-51539.Rostad and Pereira, 198630. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min

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

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1546.1Tret'yakov, 200730. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillarySE-541546.Harland, Cumming, et al., 1986He, 50. C @ 2. min, 8. K/min, 250. C @ 12. min; Column length: 25. m; Column diameter: 0.32 mm

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5260.4Donnelly, Abdel-Hamid, et al., 199330. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min
CapillaryDB-5262.33Rostad and Pereira, 198630. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

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

Sabbah and Gouali, 1994
Sabbah, R.; Gouali, M., Energetics of intra- and inter-molecular bonds in the three nitrophenols, Aust. J. Chem., 1994, 47, 1651-1660. [all data]

Finch, Gardner, et al., 1983
Finch, A.; Gardner, P.J.; Wu, D., Studies on nitrophenols. Part IV. The standard enthalpies of combustion and formation of 1,2-dihydroxybenzene, 1,2- and 1,4-nitrophenol, Thermochim. Acta, 1983, 66, 333-342. [all data]

Rinkenbach, 1930
Rinkenbach, W.H., The heats of combustion and formation of aromatic nitro compounds, J. Am. Chem. Soc., 1930, 52, 115-120. [all data]

Swarts, 1914
Swarts, F., Sur la chaleur de combustion de quelques derives nitres aromatlques, Recl. Trav. Chim. Pays-Bas, 1914, 33, 281-298. [all data]

Garner and Abernethy, 1921
Garner, W.E.; Abernethy, C.L., Heats of combustion and formation of nitro-compounds. Part I. - Benzene, toluene, phenol and methylaniline series, Proc. Roy. Soc. London A, 1921, 213-235. [all data]

Campbell and Campbell, 1941
Campbell, A.N.; Campbell, A.J.R., The system naphthalene-p-nitrophenol: an experimental investigation of all the variables in an equation of the freezing point curve, Can. J. Res., 1941, B19, 73-79. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Sabbah and Gouali, 1994, 2
Sabbah, R.; Gouali, M., Energetics of Intra- and Inter-molecular Bonds in the Three Nitrophenols, Aust. J. Chem., 1994, 47, 9, 1651-621, https://doi.org/10.1071/CH9941651 . [all data]

Parsons, Rochester, et al., 1971
Parsons, G.H.; Rochester, C.H.; Wood, C.E.C., Effect of 4-substitution on the thermodynamics of hydration of phenol and the phenoxide anion, J. Chem. Soc., B:, 1971, 533, https://doi.org/10.1039/j29710000533 . [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Trieschmann, 1935
Trieschmann, H.G., , Ph.D. Dissertation, Inst. Fur Phys. Chem. and Electrochem. der Universitat Kiel, Germany, 1935. [all data]

Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.Z., Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Singh and Kumar, 1986
Singh, N.B.; Kumar, P., Solidification behavior of the cinnamic acid-p-nitrophenol eutectic system, J. Chem. Eng. Data, 1986, 31, 406-408. [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]

Musuc, Razus, et al., 2002
Musuc, A.M.; Razus, D.; Oancea, D., Analele Universitatii Bucuresti Chimie, 2002, 11, 2, 147. [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]

Booss and Hauschildt, 1972
Booss, H.J.; Hauschildt, K.R., Die Schmelzenthalpie des Benzils und 4-Nitrophenols, Z. Anal. Chem., 1972, 261(1), 32. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [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]

Kobayashi and Nagakura, 1975
Kobayashi, T.; Nagakura, S., Photoelectron spectra of nitrophenols and nitroanisoles, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 421. [all data]

Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A., Effects of induction and resonance in the calculation of ionization potentials of substituted benzenes by perturbation molecular orbital theory, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 36. [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]

Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L., Effect of substituent groups on the ionization potentials of benzenes, J. Phys. Chem., 1962, 66, 436. [all data]

Grammaticakis, 1951
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'ultraviolet moyen et le visible des arylamines isomeres et de leurs derives N substitues (Premier memoire), Bull. Soc. Chim. Fr., 1951, 18, 220-226. [all data]

Erdmann, Rochholz, et al., 1992
Erdmann, F.; Rochholz, G.; Schütz, H., Retention-indices on OV-1 of approximately 170 commonly used pesticides, Mikrochim. Acta, 1992, 106, 3-6, 219-226, https://doi.org/10.1007/BF01242093 . [all data]

Verevkin, Belen'kaya, et al., 1990
Verevkin, S.P.; Belen'kaya, R.S.; Rozhnov, A.M.; Matyushina, V.P., Investigation of the chromatographic behaviour of alkylnitrophenols, Zh. Anal. Khim., 1990, 45, 1786-1790. [all data]

Mitchell and Vernon, 1972
Mitchell, P.T.; Vernon, F., Gas-Liquid Chromatography of Nitrophenols and Methyl Derivatives, J. Chromatogr., 1972, 65, 3, 487-491, https://doi.org/10.1016/S0021-9673(00)84994-8 . [all data]

Van Durme, Dewulf, et al., 2007
Van Durme, J.; Dewulf, J.; Sysmans, W.; Leys, C.; Van Langenhove, H., Abatement and degradation pathways of toluene in indoor air by positive corona discharge, Chemosphere, 2007, 68, 10, 1821-1829, https://doi.org/10.1016/j.chemosphere.2007.03.053 . [all data]

Ferchichi and Messadi, 1994
Ferchichi, L.; Messadi, D., Simulations de la rétention et de l'effecacité de colonne en chromatographie en phase gazeuse à température programmée: théorie et application, Analusis, 1994, 22, 392-399. [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

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

Harland, Cumming, et al., 1986
Harland, B.J.; Cumming, R.I.; Gillings, E., The Kovats indexes of some organic micropollutants on an SE54 capillary column, EUR, I Org. Micropollut. Aquat. Environ., 1986, EUR 10388, 123-127. [all data]

Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F., Application of gas chromatographic retention properties to the identification of environmental contaminants, J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References