Picric acid

• Formula: C₆H₃N₃O₇
• Molecular weight: 229.1039
• IUPAC Standard InChI: InChI=1S/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H Copy

  
• IUPAC Standard InChIKey: OXNIZHLAWKMVMX-UHFFFAOYSA-N Copy
• CAS Registry Number: 88-89-1
• 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: Phenol, 2,4,6-trinitro-; C.I. 10305; Carbazotic Acid; Melinite; Nitroxanthic acid; Picral; Picronitric acid; Trinitrophenol; 2,4,6-Trinitrophenol; Acide picrique; Acido picrico; Phenol trinitrate; Pikrinezuur; Pikrinsaeure; Pikrynowy kwas; 1,3,5-Trinitrophenol; 2-Hydroxy-1,3,5-trinitrobenzene; 2,4,6-Trinitrofenol; 2,4,6-Trinitrofenolo; Kyselina pikrova; UN 0154; 2,4,6-Trinitrophenyl; Hager's reagent; Pertite; Reflorit; NSC 36947
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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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

Constant pressure heat capacity of solid

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

C₆H₂N₃O₇^- +  =

By formula: C₆H₂N₃O₇^- + H⁺ = C₆H₃N₃O₇

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

De-protonation reactions

C₆H₂N₃O₇^- +  =

By formula: C₆H₂N₃O₇^- + H⁺ = C₆H₃N₃O₇

References

Go To: Top, Condensed phase thermochemistry 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]

Vorob'yov, Privalova, et al., 1960
Vorob'yov, A.F.; Privalova, N.M.; Storozhenko, L.V.; Skuratov, S.M., Standard enthalpies of formation of some picrates, Dokl. Akad. Nauk SSSR, 1960, 135, 1131-1132. [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]

Taylor and Rinkenbach, 1924
Taylor, C.A.; Rinkenbach, W.H., The specific heats of trinitrotoluene, tetryl, picric acid and their molecular complexes, J. Am. Chem. Soc., 1924, 46, 1504-1510. [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]

Leito, Raamat, et al., 2009
Leito, I.; Raamat, E.; Kutt, A.; Saame, J.; Kipper, K.; Koppel, I.A.; Koppel, I.; Zhang, M.; Mishima, M.; Yagupolskii, L.M.; Garlyauskayte, R.Y.; Filatov, A.A., Revision of the Gas-Phase Acidity Scale below 300 kcal mol(-1), J. Phys. Chem. A, 2009, 113, 29, 8421-8424, https://doi.org/10.1021/jp903780k . [all data]

Dzidic, Carroll, et al., 1974
Dzidic, I.; Carroll, D.I.; Stillwell, R.N.; Horning, E.C., Gas phase reactions. Ionization by proton transfer to superoxide anions, J. Am. Chem. Soc., 1974, 96, 5258. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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