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Picric acid

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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-217.9 ± 2.0kJ/molCcbFinch and Smith, 1983ALS
Deltafsolid-214.0 ± 1.3kJ/molCcbVorob'yov, Privalova, et al., 1960ALS
Deltafsolid-224.9kJ/molCcbRinkenbach, 1930Author hf298_condensed[kcal/mol]=-55.98; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-2570. ± 30.kJ/molAVGN/AAverage of 8 values; Individual data points

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
239.7293.Taylor and Rinkenbach, 1924T = 90 to 395 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:
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
Tfus395. ± 1.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Deltasub105.1 ± 1.6kJ/molMECundall, Frank Palmer, et al., 1978Based on data from 314. - 406. K.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
106.4483.AStephenson and Malanowski, 1987The value of 106.4 kJ/mole from Stephenson and Malanowski, 1987 is likely an enthalpy of sublimation; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
17.100394.1Farrell, Shahidi, et al., 1979DH
17.1394.1Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
43.4394.1Farrell, Shahidi, et al., 1979DH

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 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- + Hydrogen cation = Picric acid

By formula: C6H2N3O7- + H+ = C6H3N3O7

Quantity Value Units Method Reference Comment
Deltar1298. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.
Quantity Value Units Method Reference Comment
Deltar1267. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.
Deltar<1292.9kJ/molIMRBDzidic, Carroll, et al., 1974gas phase; I- deprotonates

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- + Hydrogen cation = Picric acid

By formula: C6H2N3O7- + H+ = C6H3N3O7

Quantity Value Units Method Reference Comment
Deltar1298. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.
Quantity Value Units Method Reference Comment
Deltar1267. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.
Deltar<1292.9kJ/molIMRBDzidic, Carroll, et al., 1974gas phase; I- deprotonates

IR 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: Coblentz Society, Inc.

Spectrum

A digitized version of this spectrum is not currently available.

Additional Data

View scan of original (hardcopy) spectrum.

Owner COBLENTZ SOCIETY
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Source reference COBLENTZ NO. 1222
Date Not specified, most likely prior to 1970
Instrument Not specified, most likely a prism, grating, or hybrid spectrometer.
Data processing (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


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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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-IW-2594
NIST MS number 243411

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.


References

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

Cundall, Frank Palmer, et al., 1978
Cundall, Robert B.; Frank Palmer, T.; Wood, Colin E.C., Vapour pressure measurements on some organic high explosives, J. Chem. Soc., Faraday Trans. 1, 1978, 74, 0, 1339, https://doi.org/10.1039/f19787401339 . [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]

Farrell, Shahidi, et al., 1979
Farrell, P.G.; Shahidi, F.; Casellato, F.; Vecchi, C.; Girelli, A., DSC studies of aromatic hydrocarbon picrates, Thermochim. Acta, 1979, 33, 275-280. [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]

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

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