Phenol, 2,4-dinitro-

• Formula: C₆H₄N₂O₅
• Molecular weight: 184.1064
• IUPAC Standard InChI: InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H Copy

  
• IUPAC Standard InChIKey: UFBJCMHMOXMLKC-UHFFFAOYSA-N Copy
• CAS Registry Number: 51-28-5
• 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: α-Dinitrophenol; Aldifen; Fenoxyl Carbon N; Nitrophen; Nitrophene; Phenol, α-dinitro-; Solfo Black B; Solfo Black BB; Solfo Black G; Solfo Black SB; Solfo Black 2B Supra; Tertrosulphur Black PB; Tertrosulphur PBR; 1-Hydroxy-2,4-dinitrobenzene; 2,4-Dinitrophenol; 2,4-DNP; Chemox PE; Dinitrofenolo; Dinitrophenol; DNP; EK 102; Nitro kleenup; NSC 1532; X 32; 2,4-Dinitrofenol; Dinofan; Maroxol-50; Rcra waste number P048; Tertrosulfur black pb; Tertrosulfur PBR
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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

C₆H₃N₂O₅^- +  =

By formula: C₆H₃N₂O₅^- + H⁺ = C₆H₄N₂O₅

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₆H₃N₂O₅^- +  =

By formula: C₆H₃N₂O₅^- + H⁺ = C₆H₄N₂O₅

References

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

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

Finch and Smith, 1983
Finch, A.; Smith, A.E., Thermochemistry of nitrophenols. V. Enthalpies of formation of 2,4- and 2,6-dinitrophenols, Thermochim. Acta, 1983, 69, 375-378. [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]

Badoche, 1942
Badoche, M., Chaleurs de combustion de derives nitres phenoliques, Bull. Soc. Chim. France, 1942, 9, 86-95. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Burlot, 1939
Burlot, E., Etude relative a la calorimetrie des explosifs, Mem. Poudres, 1939, 29, 226-260. [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]

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]

Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W., Z. Elektrochem., 1958, 62, 61. [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Hoyer and Peperle, 1958, 2
Hoyer, H.; Peperle, W., Dampfdrunkmessungen an organischen substanzen und ihre sublimationswarmen, Z. Electrochem., 1958, 62, 61-66. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]

Koppel, Taft, et al., 1994
Koppel, I.A.; Taft, R.W.; Anvia, F.; Zhu, S.Z.; Hu, L.Q.; Sung, K.S.; Desmarteau, D.D.; Yagupolskii, L.M., The Gas-Phase Acidities of Very Strong Neutral Bronsted Acids, J. Am. Chem. Soc., 1994, 116, 7, 3047, https://doi.org/10.1021/ja00086a038 . [all data]

Dougherty, Younathan, et al., 1978
Dougherty, D.; Younathan, E.S.; Voll, R.; Abdulnur, S.; McGlynn, S.P., Photoelectron spectroscopy of some biological molecules, J. Electron Spectrosc. Relat. Phenom., 1978, 13, 379. [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation

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