Benzene, nitro-
- Formula: C6H5NO2
- Molecular weight: 123.1094
- IUPAC Standard InChIKey: LQNUZADURLCDLV-UHFFFAOYSA-N
- CAS Registry Number: 98-95-3
- 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. - Isotopologues:
- Other names: Essence of Mirbane; Essence of Myrbane; Mirbane oil; Nitrobenzene; Nitrobenzol; Oil of Mirbane; Oil of Myrbane; Nitrobenzeen; Nitrobenzen; NCI-C60082; Rcra waste number U169; UN 1662; NSC 9573
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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 16.38 ± 0.16 | kcal/mol | Ccb | Lebedeva, Katin, et al., 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 15.72 ± 0.10 kcal/mol |
Phase change data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tboil | 484. ± 2. | K | AVG | N/A | Average of 24 out of 25 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 278.9 ± 0.2 | K | AVG | N/A | Average of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.0 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 313. to 353. K.; AC |
ΔvapH° | 13.148 ± 0.0043 | kcal/mol | C | Kusano and Wadso, 1971 | ALS |
ΔvapH° | 13.1 | kcal/mol | N/A | Kusano and Wadsö, 1971 | AC |
ΔvapH° | 13.4 ± 0.41 | kcal/mol | ME | Lebedeva, Katin, et al., 1971, 2 | Based on data from 291. to 305. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.1 | 287. | A | Stephenson and Malanowski, 1987 | Based on data from 279. to 296. K. See also Dykyj, 1972 and Lynch and Wilke, 1960.; AC |
13.0 | 303. | N/A | Zaraiskii, 1985 | Based on data from 288. to 318. K.; AC |
13.4 ± 0.10 | 291. | V | Lebedeva, Katin, et al., 1971 | ALS |
12.5 | 293. | ME | Sklyarenko, Markin, et al., 1958 | Based on data from 283. to 303. K.; AC |
11.6 | 422. | N/A | Oliver and Grisard, 1952 | Based on data from 407. to 483. K. See also Boublik, Fried, et al., 1984.; AC |
11.7 | 425. | N/A | Toral and Moles, 1933 | Based on data from 369. to 481. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
407.3 to 483.78 | 4.20982 | 1727.592 | -73.438 | Brown, 1952 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.897 | 278.8 | Domalski and Hearing, 1996 | AC |
2.5848 | 278.9 | Pacor, 1967 | DH |
2.8970 | 278.8 | Parks, Todd, et al., 1936 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.27 | 278.9 | Pacor, 1967 | DH |
10.39 | 278.8 | Parks, Todd, et al., 1936 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.94 ± 0.08 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 191.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 183.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.000 ± 0.010 | LPES | Desfrancois, Periquet, et al., 1999 | B |
1.01 ± 0.10 | TDEq | Chowdhury, Heinis, et al., 1986 | ΔGea(423 K) = -22.8 kcal/mol; ΔSea = -1.0 eu.; B |
1.00 ± 0.060 | TDAs | Chen, Wiley, et al., 1994 | B |
1.00 ± 0.020 | ECD | Chen, Chen, et al., 1992 | B |
1.019 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -23.1 kcal/mol; ΔSea =-1.0, est. from data in Chowdhury, Heinis, et al., 1986; B |
<1.180 ± 0.050 | PD | Mock and Grimsrud, 1989 | B |
<1.09997 | IMRB | Henglein and Muccini, 1959 | EA: < SO2; B |
>0.70 ± 0.20 | Endo | Lifshitz, Tiernan, et al., 1973 | B |
>0.39999 | ES | Compton, Christophorou, et al., 1966 | B |
Ionization energy determinations
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 12.63 ± 0.15 | C2H2+CO+NO | PIPECO | Nishimura, Das, et al., 1986 | LBLHLM |
C4H3+ | 15.66 ± 0.15 | C2H2+NO2 | PIPECO | Nishimura, Das, et al., 1986 | LBLHLM |
C4H3+ | 11.40 ± 0.05 | NO+C2H2O | PIPECO | Panczel and Baer, 1984 | T = 298K; LBLHLM |
C4H3+ | 11.54 ± 0.05 | NO+C2H2O | PIPECO | Panczel and Baer, 1984 | T = 0K; LBLHLM |
C4H3+ | 16.31 ± 0.08 | ? | EI | Allam, Migahed, et al., 1982 | LBLHLM |
C5H5+ | 11.08 ± 0.16 | CO+NO | PIPECO | Nishimura, Das, et al., 1986 | LBLHLM |
C5H5+ | 11.30 ± 0.05 | CO+NO | PIPECO | Panczel and Baer, 1984 | T = 298K; LBLHLM |
C5H5+ | 11.44 ± 0.05 | CO+NO | PIPECO | Panczel and Baer, 1984 | T = 0K; LBLHLM |
C6H5+ | 11.51 ± 0.35 | NO2 | CAD | Katritzky, Watson, et al., 1990 | LL |
C6H5+ | 11.08 ± 0.16 | NO2 | PIPECO | Nishimura, Das, et al., 1986 | LBLHLM |
C6H5+ | 11.14 ± 0.05 | NO2 | PIPECO | Panczel and Baer, 1984 | T = 298K; LBLHLM |
C6H5+ | 11.28 ± 0.05 | NO2 | PIPECO | Panczel and Baer, 1984 | T = 0K; LBLHLM |
C6H5+ | 12.14 ± 0.08 | NO2 | EI | Allam, Migahed, et al., 1982 | LBLHLM |
C6H5+ | 9.46 ± 0.05 | NO2 | PI | Matyuk, Potapov, et al., 1979 | LLK |
C6H5+ | 11.9 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
C6H5+ | 12.16 | ? | EI | Howe and Williams, 1969 | RDSH |
C6H5O+ | 10.68 ± 0.35 | NO | CAD | Katritzky, Watson, et al., 1990 | LL |
C6H5O+ | 10.89 ± 0.04 | NO | PIPECO | Nishimura, Das, et al., 1986 | LBLHLM |
C6H5O+ | 10.98 ± 0.05 | NO | PIPECO | Panczel and Baer, 1984 | T = 298K; LBLHLM |
C6H5O+ | 11.12 ± 0.05 | NO | PIPECO | Panczel and Baer, 1984 | T = 0K; LBLHLM |
C6H5O+ | 10.95 ± 0.05 | NO | PI | Matyuk, Potapov, et al., 1979 | LLK |
C6H5O+ | 10.4 ± 0.1 | NO | EI | Brown, 1970 | RDSH |
NO+ | 10.89 ± 0.04 | C6H5O | PIPECO | Nishimura, Das, et al., 1986 | LBLHLM |
NO+ | 11.18 ± 0.05 | C6H5O | PIPECO | Panczel and Baer, 1984 | T = 0K; LBLHLM |
NO+ | 11.04 ± 0.05 | C6H5O | PIPECO | Panczel and Baer, 1984 | T = 298K; LBLHLM |
De-protonation reactions
C6H4NO2- + =
By formula: C6H4NO2- + H+ = C6H5NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 377.0 ± 3.1 | kcal/mol | G+TS | Cheng and Grabowski, 1989 | gas phase; between EtOH, iPrOH; B |
ΔrH° | 354.2 ± 3.1 | kcal/mol | G+TS | Meot-ner and Kafafi, 1988 | gas phase; acidity stronger than all levels of computation by 25 kcal/mol; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 369.3 ± 3.0 | kcal/mol | IMRB | Cheng and Grabowski, 1989 | gas phase; between EtOH, iPrOH; B |
ΔrG° | 346.5 ± 3.0 | kcal/mol | IMRB | Meot-ner and Kafafi, 1988 | gas phase; acidity stronger than all levels of computation by 25 kcal/mol; B |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lebedeva, Katin, et al., 1971
Lebedeva, N.D.; Katin, Y.A.; Akhmedova, G.Y.,
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Kusano and Wadsö, 1971
Kusano, Kazuhito; Wadsö, Ingemar,
Enthalpy of Vaporization of Some Organic Substances at 25.0°C and Test of Calorimeter,
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Electron Binding to Valence and Multipole states of Molecules: Nitrobenzene, para- and meta-dinitrobenzenes,
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Electron-impact ionization and appearance potentials,
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Photoelectron spectra of substituted benzenes,
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On the dissociation dynamics of energy-selected nitrobenzene ion,
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A photoelectron photoion coincidence (PEPICO) study of fragmentation rates and linetic energy release distributions in nitrobenzene,
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Katritzky, Watson, et al., 1990
Katritzky, A.R.; Watson, C.H.; Dega-Szafran, Z.; Eyler, J.R.,
Collisionally activated dissociation of N-alkylpyridinium cations to pyridine and alkyl cations in the gas phase,
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Cheng, X.; Grabowski, J.J.,
Gas-phase Acidity of Nitrobenzene from Flowing Afterglow Bracketing Studies,
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Carbon Acidities of Aromatic Compounds,
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. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas 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 ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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