1,3,5-Trinitrobenzene
- Formula: C6H3N3O6
- Molecular weight: 213.1045
- IUPAC Standard InChIKey: UATJOMSPNYCXIX-UHFFFAOYSA-N
- CAS Registry Number: 99-35-4
- 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: Benzene,1,3,5-trinitro-; s-Trinitrobenzene; syn-Trinitrobenzene; Trinitrobenzeen; Trinitrobenzene; Trinitrobenzol; TNB; Rcra waste number U234; NSC 36931; sym-Trinitrobenzene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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:
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 | -37. ± 1. | kJ/mol | Ccb | Lebedeva, Ryadnenko, et al., 1971 | Hfusion=4.0±0.1; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2753. ± 0.4 | kJ/mol | Ccb | Lebedeva, Ryadnenko, et al., 1971 | Hfusion=4.0±0.1; ALS |
ΔcH°solid | -2745.9 ± 2.8 | kJ/mol | Ccb | Badoche, 1939 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2750.9 kJ/mol; ALS |
ΔcH°solid | -2746.8 ± 2.8 | kJ/mol | Ccb | Burlot, 1939 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2763.0 kJ/mol; ALS |
ΔcH°solid | -2785. | kJ/mol | Ccb | Garner and Abernethy, 1921 | ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
214.6 | 298.15 | Radomska and Radomski, 1980 | T = 180 to 400 K. Data given graphically; Cp calculated from equation. Thermodynamically stable modification I.; DH |
222.7 | 298.15 | Radomska and Radomski, 1980 | T = 180 to 380 K. Data given graphically; Cp calculated from equation. Metastable modification II.; 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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 394.2 | K | N/A | Hwang, Tamura, et al., 1990 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 398.4 | K | N/A | Radomska and Radomski, 1980, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 396.15 | K | N/A | Waclawek and Hurwic, 1967 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 397.7 | K | N/A | Jones and Neuworth, 1944 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 107.3 ± 0.6 | kJ/mol | ME | Cundall, Frank Palmer, et al., 1978 | Based on data from 313. to 395. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
70.3 | 490. | A | Stephenson and Malanowski, 1987 | Based on data from 475. to 585. K. See also Maksimov, 1968 and Dykyj, 1972.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.81 | 380.3 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.13 | 370. | Domalski and Hearing, 1996 | CAL |
38.95 | 380.3 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
15.000 | 398.4 | crystaline, I | liquid | Radomska and Radomski, 1980 | DH |
1.900 | 370. | crystaline, II | crystaline, I | Radomska and Radomski, 1980 | DH |
14.800 | 380.3 | crystaline, I | liquid | Radomska and Radomski, 1980 | DH |
13.200 | 383.0 | crystaline, I | liquid | Radomska and Radomski, 1980 | Metastable modification III.; DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
37.7 | 398.4 | crystaline, I | liquid | Radomska and Radomski, 1980 | DH |
5.13 | 370. | crystaline, II | crystaline, I | Radomska and Radomski, 1980 | DH |
38.9 | 380.3 | crystaline, I | liquid | Radomska and Radomski, 1980 | DH |
34.5 | 383.0 | crystaline, I | liquid | Radomska and Radomski, 1980 | Metastable; 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - 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
By formula: Br- + C6H3N3O6 = (Br- • C6H3N3O6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrS° | 92. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; 1,3,5-trinitrobenzene, Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 54.8 ± 4.2 | kJ/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° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
54.8 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; 1,3,5-trinitrobenzene, Entropy change calculated or estimated; M |
Gas Chromatography
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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
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 284.47 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
Capillary | DB-5MS | 287.18 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C |
Capillary | DB-5MS | 285.91 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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]
Badoche, 1939
Badoche, M.M.,
Determinations des chaleurs de combustion de derives nitres de la serie benzenique,
Bull. Soc. Chim. France, 1939, 6, 570-579. [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]
Radomska and Radomski, 1980
Radomska, M.; Radomski, R.,
Calorimetric studies of binary systems of 1,3,5-trinitrobenzene with naphthalene, anthracene, and carbazole. I. Phase transitions and heat capacities of the pure components and charge-transfer complexes,
Thermochim. Acta, 1980, 40, 405-414. [all data]
Hwang, Tamura, et al., 1990
Hwang, D.-R.; Tamura, M.; Yoshida, T.; Tanaka, N.; Hosoya, F.,
Estimation of ΔH°f of nitro derivatives of benzene and toluene using AM1 and DSC,
J. Energ. Mater., 1990, 8, 85-98. [all data]
Radomska and Radomski, 1980, 2
Radomska, M.; Radomski, R.,
Calorimetric Studies of Binary Systems of 1,3,5-Trinitrobenzene with Naphthalene, Anthracene, and Carbazole I. Phase Transitions and Heat Capacities of the Pure COmponents and Charge Transfer Complex,
Thermochim. Acta, 1980, 40, 405-14. [all data]
Waclawek and Hurwic, 1967
Waclawek, Z.; Hurwic, J.,
Dipole moment and spectroscopic studies of the 1,3,5-trinitrobenzene complexes with some pyridine derivatives in nonpolar solvents,
Rocz. Chem., 1967, 41, 1993. [all data]
Jones and Neuworth, 1944
Jones, R.C.; Neuworth, M.B.,
The Ultraviolet Absorption Spectra of Hydrocarbon-Trinitrobenzene Complexes,
J. Am. Chem. Soc., 1944, 66, 1497. [all data]
Cundall, Frank Palmer, et al., 1978
Cundall, Robert B.; Frank Palmer, T.; Wood, Colin E.C.,
Vapour pressure measurements on some organic high explosives,
J. Chem. Soc., Faraday Trans. 1, 1978, 74, 0, 1339, https://doi.org/10.1039/f19787401339
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Maksimov, 1968
Maksimov, Y.Y.,
Russ. J. Phys. Chem., 1968, 42, 11, 1550. [all data]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [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]
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]
Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid T Temperature Tfus Fusion (melting) point ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔrS° Entropy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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