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
- IUPAC Standard InChIKey: UFBJCMHMOXMLKC-UHFFFAOYSA-N
- 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
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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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -56.29 | kcal/mol | Ccb | Finch and Smith, 1983 | |
| ΔfH°solid | -53.31 | kcal/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-55.57 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -644.65 ± 0.76 | kcal/mol | Ccb | Finch and Smith, 1983 | |
| ΔcH°solid | -644.58 ± 0.64 | kcal/mol | Ccb | Badoche, 1942 | Reanalyzed by Cox and Pilcher, 1970, Original value = -645.27 kcal/mol |
| ΔcH°solid | -646.05 ± 0.64 | kcal/mol | Ccb | Burlot, 1939 | Reanalyzed by Cox and Pilcher, 1970, Original value = -648.80 kcal/mol |
| ΔcH°solid | -647.629 | kcal/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-55.57 |
| ΔcH°solid | -650.2 | kcal/mol | Ccb | Garner and Abernethy, 1921 |
Reaction thermochemistry data
Go To: Top, Condensed phase 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 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 316.0 ± 2.1 | kcal/mol | G+TS | Koppel, Taft, et al., 1994 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 308.6 ± 2.0 | kcal/mol | IMRE | Koppel, Taft, et al., 1994 | gas phase |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
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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