Benzoic acid, 4-nitro-
- Formula: C7H5NO4
- Molecular weight: 167.1189
- IUPAC Standard InChIKey: OTLNPYWUJOZPPA-UHFFFAOYSA-N
- CAS Registry Number: 62-23-7
- 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: Benzoic acid, p-nitro-; p-Nitrobenzoic acid; Nitrodracylic acid; 4-Nitrobenzoic acid; Kyselina p-nitrobenzoova; 1-Carboxy-4-nitrobenzene; 4-Nitrodracylic acid; p-Nitrobenzenecarboxylic acid; p-Nitrodracylic acid; NSC 7707
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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 | -102.1 ± 0.2 | kcal/mol | Ccb | Lebedeva, Ryadnenko, et al., 1971 | Hfusion=8.3±0.3, see Lebedeva, Rjadnenko, et al., 1969; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -727.1 ± 0.2 | kcal/mol | Ccb | Lebedeva, Ryadnenko, et al., 1971 | Hfusion=8.3±0.3, see Lebedeva, Rjadnenko, et al., 1969; ALS |
ΔcH°solid | -728.908 | kcal/mol | Ccb | Verkade, 1926 | ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.30 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100 C. Mean value.; DH |
43.09 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 245 C.; DH |
43.69 | 297.9 | Andrews, 1926 | T = 110 to 344 K. Value is unsmoothed experimental datum.; 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 | 512.35 | K | N/A | Booss and Hauschildt, 1972 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 512.4 | K | N/A | Andrews, Lynn, et al., 1926, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 507. | K | N/A | Johnson and Guest, 1910 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 28.6 ± 0.1 | kcal/mol | ME | Ribeiro da Silva, 1999 | AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
27.6 ± 0.1 | 374. | ME | Ribeiro da Silva, 1999 | Based on data from 367. to 381. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.82 | 512.4 | Domalski and Hearing, 1996 | AC |
8.8193 | 512.35 | Booss and Hauschildt, 1972 | DH |
8.8193 | 512.4 | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.2 | 512.35 | Booss and Hauschildt, 1972 | DH |
17.2 | 512.4 | Andrews, Lynn, et al., 1926 | 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
C7H4NO4- + =
By formula: C7H4NO4- + H+ = C7H5NO4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 328.1 ± 2.2 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 321.1 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase |
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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.2 ± 0.2 | EI | Benoit, 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H4NO3+ | 11.6 ± 0.2 | OH | EI | Benoit, 1973 | LLK |
De-protonation reactions
C7H4NO4- + =
By formula: C7H4NO4- + H+ = C7H5NO4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 328.1 ± 2.2 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 321.1 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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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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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 290676 |
UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Grammaticakis, 1951 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 205 |
Instrument | n.i.g. |
Melting point | 242 |
Boiling point | sub |
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), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lebedeva, Ryadnenko, et al., 1971
Lebedeva, N.D.; Ryadnenko, V.L.; Kuznetsova, I.N.,
Heats of combustion and enthalpies of formation of certain aromatic nitro-derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 549. [all data]
Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M.,
Heats of formation of some N-containing organic compounds,
Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [all data]
Verkade, 1926
Verkade, P.E.,
Verbrandingswarmten van plaatsings-isomere benzol-derivaten en de theorie der geinduceerde alterneeren de polatiteit,
Verslag Akad. Wetenschappen Amsterdam, 1926, 35, 492-504. [all data]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (1), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 197-203. [all data]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Andrews, 1926
Andrews, D.H.,
The specific heats of some isomers of the type ortho, meta and para C6H4XY from 110 to 340K,
J. Am. Chem. Soc., 1926, 48, 1287-1298. [all data]
Booss and Hauschildt, 1972
Booss, H.J.; Hauschildt, K.R.,
Die Schmelzenthalpie des Benzils und 4-Nitrophenols,
Z. Anal. Chem., 1972, 261(1), 32. [all data]
Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J.,
The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds,
J. Am. Chem. Soc., 1926, 48, 1274. [all data]
Johnson and Guest, 1910
Johnson, T.B.; Guest, H.H.,
J. Am. Chem. Soc., 1910, 32, 761. [all data]
Ribeiro da Silva, 1999
Ribeiro da Silva, M.,
Enthalpies of combustion, vapour pressures, and enthalpies of sublimation of three methoxy-nitrobenzoic acids. Vapour pressures and enthalpies of sublimation of the three nitrobenzoic acids,
The Journal of Chemical Thermodynamics, 1999, 31, 11, 1429-1441, https://doi.org/10.1006/jcht.1999.0507
. [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]
Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G.,
Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase,
Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005
. [all data]
Benoit, 1973
Benoit, F.,
Substituent effects in mass spectrometry. III. Substituent effects in the dissociation of the molecular ions of para and meta subtituted benzoic acids,
Org. Mass Spectrom., 1973, 7, 295. [all data]
Grammaticakis, 1951
Grammaticakis, P.,
Contribution a l'etude de l'absorption dans l'ultraviolet moyen et le visible des arylamines isomeres et de leurs derives N substitues (Premier memoire),
Bull. Soc. Chim. Fr., 1951, 18, 220-226. [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), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy 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 ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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