Picric acid
- Formula: C6H3N3O7
- Molecular weight: 229.1039
- IUPAC Standard InChIKey: OXNIZHLAWKMVMX-UHFFFAOYSA-N
- 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
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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 |
---|---|---|---|---|---|
ΔfH°solid | -217.9 ± 2.0 | kJ/mol | Ccb | Finch and Smith, 1983 | ALS |
ΔfH°solid | -214.0 ± 1.3 | kJ/mol | Ccb | Vorob'yov, Privalova, et al., 1960 | ALS |
ΔfH°solid | -224.9 | kJ/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-55.98; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2570. ± 30. | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
239.7 | 293. | Taylor and Rinkenbach, 1924 | T = 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 |
---|---|---|---|---|---|
Tfus | 395. ± 1. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 105.1 ± 1.6 | kJ/mol | ME | Cundall, Frank Palmer, et al., 1978 | Based on data from 314. to 406. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
106.4 | 483. | A | Stephenson and Malanowski, 1987 | The value of 106.4 kJ/mole from Stephenson and Malanowski, 1987 is likely an enthalpy of sublimation; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.100 | 394.1 | Farrell, Shahidi, et al., 1979 | DH |
17.1 | 394.1 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
43.4 | 394.1 | Farrell, Shahidi, et al., 1979 | DH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1298. ± 9.2 | kJ/mol | G+TS | Koppel, Taft, et al., 1994 | gas 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 |
ΔrG° | 1267. ± 8.4 | kJ/mol | IMRE | Koppel, Taft, et al., 1994 | gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol. |
ΔrG° | <1292.9 | kJ/mol | IMRB | Dzidic, Carroll, et al., 1974 | gas 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- + =
By formula: C6H2N3O7- + H+ = C6H3N3O7
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1298. ± 9.2 | kJ/mol | G+TS | Koppel, Taft, et al., 1994 | gas 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 |
ΔrG° | 1267. ± 8.4 | kJ/mol | IMRE | Koppel, Taft, et al., 1994 | gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol. |
ΔrG° | <1292.9 | kJ/mol | IMRB | Dzidic, Carroll, et al., 1974 | gas 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) |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, NIST Subscription Links, 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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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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-IW-2594 |
NIST MS number | 243411 |
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), NIST Subscription Links, 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
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- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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 at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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