Benzene, 1-chloro-3-nitro-
- Formula: C6H4ClNO2
- Molecular weight: 157.554
- IUPAC Standard InChIKey: KMAQZIILEGKYQZ-UHFFFAOYSA-N
- CAS Registry Number: 121-73-3
- 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. - Other names: m-Chloronitrobenzene; m-Nitrochlorobenzene; 1-Chloro-3-nitrobenzene; 3-Chloro-1-nitrobenzene; Chloro-m-nitrobenzene; 3-Chloronitrobenzene; Nitrochlorobenzene, meta-; Metachloronitrobenzene; NSC 5502
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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°solid | -14.10 | kcal/mol | Ccb | Masalitinova, Oleinikova, et al., 1981 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -692.9 ± 0.6 | kcal/mol | Ccb | Masalitinova, Oleinikova, et al., 1981 |
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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 508.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 508.65 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 317. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 316.3 | K | N/A | Sidgwick and Rubie, 1921 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 317. | K | N/A | Buechner, 1906 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 316.95 | K | N/A | Bruner, 1894 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.4 ± 0.05 | kcal/mol | GS | Verevkin and Schick, 2003 | Based on data from 319. to 364. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.7 ± 0.36 | kcal/mol | C | Ribeiro da Silva, Lobo Ferreira, et al., 2009 | AC |
ΔsubH° | 19.4 ± 0.07 | kcal/mol | GS | Verevkin and Schick, 2003 | Based on data from 281. to 314. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.3 | 429. | EB | Putcha, Ivaturi, et al., 1984 | Based on data from 414. to 506. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
17.9 ± 0.5 | 281. | V | Wolf and Weghofer, 1938 | ALS |
17.9 ± 0.41 | 275. to 286. | N/A | Trieschmann, 1935 | See also Wolf and Weghofer, 1938, 2.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.665 | 316.9 | Straka, Ruzicka, et al., 2007 | AC |
4.457 | 318. | Verevkin and Schick, 2003 | AC |
4.630 | 317.6 | Acree, 1991 | AC |
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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: Br- + C6H4ClNO2 = (Br- • C6H4ClNO2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.5 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 8.1 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
8.1 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
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:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.28 ± 0.10 | IMRE | Chowdhury, Heinis, et al., 1986 | ΔGea(423 K) = -28.8 kcal/mol; ΔSea (estimated) = -1.7 eu.; B |
1.258 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
<1.380 ± 0.050 | PD | Mock and Grimsrud, 1989 | B |
1.258 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -28.4 kcal/mol; ΔSea =-1.7, est. from data in Chowdhury, Heinis, et al., 1986; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.9 ± 0.1 | EI | Brown, 1970 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H4Cl+ | 12.0 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
C6H4OCl+ | 10.3 ± 0.1 | NO | EI | Brown, 1970 | RDSH |
Ion clustering 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: Br- + C6H4ClNO2 = (Br- • C6H4ClNO2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.5 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 8.1 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
8.1 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Masalitinova, Oleinikova, et al., 1981
Masalitinova, T.N.; Oleinikova, T.P.; Ryadnenko, V.L.; Kiseleva, N.N.; Lebedeva, N.D.,
Thermal effects of the hydrogenation of chloronitrobenzenes,
J. Appl. Chem. USSR, 1981, 54, 1551-1554, In original 1799. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Lecat, 1947
Lecat, M.,
Some azeotropes of which one constituant is heterocyclic nitrogen,
Ann. Soc. Sci. Bruxelles, Ser. 1, 1947, 61, 73. [all data]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Sidgwick and Rubie, 1921
Sidgwick, N.V.; Rubie, H.E.,
The solubility and volatility of the chloro- and nitro-anilines and of their acetyl derivatives,
J. Chem. Soc., 1921, 119, 1013-24. [all data]
Buechner, 1906
Buechner, E.H.,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1906, 54, 665. [all data]
Bruner, 1894
Bruner, L.,
The heats of fusion of some organic compounds,
Ber. Dtsch. Chem. Ges., 1894, 27, 2102. [all data]
Verevkin and Schick, 2003
Verevkin, Sergey P.; Schick, Christoph,
Determination of vapor pressures, enthalpies of sublimation, enthalpies of vaporization, and enthalpies of fusion of a series of chloro-aminobenzenes and chloro-nitrobenzenes,
Fluid Phase Equilibria, 2003, 211, 2, 161-177, https://doi.org/10.1016/S0378-3812(03)00181-X
. [all data]
Ribeiro da Silva, Lobo Ferreira, et al., 2009
Ribeiro da Silva, Manuel A.V.; Lobo Ferreira, Ana I.M.C.; Moreno, Ana Rita G.,
Experimental thermochemical study of the monochloronitrobenzene isomers,
The Journal of Chemical Thermodynamics, 2009, 41, 1, 109-114, https://doi.org/10.1016/j.jct.2008.07.012
. [all data]
Putcha, Ivaturi, et al., 1984
Putcha, Sivaram; Ivaturi, Rao V.; Machiraju, Ramakrishna,
Vapor pressures of o-and m-nitrochlorobenzene,
J. Chem. Eng. Data, 1984, 29, 2, 135-136, https://doi.org/10.1021/je00036a011
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Trieschmann, 1935
Trieschmann, H.G.,
, Ph.D. Dissertation, Inst. Fur Phys. Chem. and Electrochem. der Universitat Kiel, Germany, 1935. [all data]
Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.Z.,
Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]
Straka, Ruzicka, et al., 2007
Straka, Martin; Ruzicka, Kvetoslav; Ruzicka, Vlastimil,
Heat Capacities of Chloroanilines and Chloronitrobenzenes,
J. Chem. Eng. Data, 2007, 52, 4, 1375-1380, https://doi.org/10.1021/je700080k
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P.,
Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-,
J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014
. [all data]
Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P.,
Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A- + B = A + B-,
J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037
. [all data]
Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H.,
Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase,
Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083
. [all data]
Mock and Grimsrud, 1989
Mock, R.S.; Grimsrud, E.P.,
Gas-Phase Electron Photodetachment Spectroscopy of the Molecular Anions of Nitroaromatic Hydrocarbons at Atmospheric Pressure,
J. Am. Chem. Soc., 1989, 111, 8, 2861, https://doi.org/10.1021/ja00190a020
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Brown, 1970
Brown, P.,
Kinetic studies in mass spectrometry. IX. Competing [M-NO2] and [M-NO] reactions in substituted nitrobenzenes. Approximate activation energies from ionization and appearance potentials,
Org. Mass Spectrom., 1970, 4, 533. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity T Temperature Tboil Boiling point 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation 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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