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
- 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Reaction thermochemistry data
Go To: Top, 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: 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° | 310.2 ± 2.2 | kcal/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° | 302.8 ± 2.0 | kcal/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° | <309.00 | kcal/mol | IMRB | Dzidic, Carroll, et al., 1974 | gas phase; I- deprotonates |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Reaction thermochemistry data, References
- Symbols used in this document:
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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.