Trinitrotoluene

• Formula: C₇H₅N₃O₆
• Molecular weight: 227.1311
• IUPAC Standard InChI: InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3 Copy

  
• IUPAC Standard InChIKey: SPSSULHKWOKEEL-UHFFFAOYSA-N Copy
• CAS Registry Number: 118-96-7
• 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: Benzene, 2-methyl-1,3,5-trinitro-; Toluene, 2,4,6-trinitro-; α-TNT; s-Trinitrotoluene; s-Trinitrotoluol; Tolite; Tritol; Trotyl; TNT; 2-Methyl-1,3,5-Trinitrobenzene; 2,4,6-Trinitrotoluene; sym-Trinitrotoluene; sym-Trinitrotoluol; NCI-C56155; TNT-tolite; Trojnitrotoluen; 2,4,6-Trinitrotolueen; 2,4,6-Trinitrotoluol; Tolit; Trotyl oil; 1-Methyl-2,4,6-trinitrobenzene; 2,4,6-TNT; Gradetol; NSC 36949; Tritol (explosive)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Phase change data

Go To: Top, Gas phase ion energetics 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:
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

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

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

De-protonation reactions

C₇H₄N₃O₆^- +  =

By formula: C₇H₄N₃O₆^- + H⁺ = C₇H₅N₃O₆

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Hu, Li, et al., 1990
Hu, R.; Li, J.; Liang, Y.; Wu, S.; Sun, L.; Wang, Y., Thermal behavior of 2,2,2-trinitroethyl-4,4,4-trinitrobutyrate, J. Therm. Anal., 1990, 36, 1155-60. [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]

Kotula and Rabczuk, 1985
Kotula, I.; Rabczuk, A., DTA Investigation of the Solid-Liquid Equilibrium for Mehtyl Derivatives of Naphthalene with Some Nitroaromatics, J. Therm. Anal., 1985, 30, 195. [all data]

Lenchitz and Velicky, 1970
Lenchitz, Charles; Velicky, Rodolf W., Vapor pressure and heat of sublimation of three nitrotoluenes, J. Chem. Eng. Data, 1970, 15, 3, 401-403, https://doi.org/10.1021/je60046a022 . [all data]

Taylor and Rinkenbach, 1924
Taylor, C.A.; Rinkenbach, W.H., The specific heats of trinitrotoluene, tetryl, picric acid, and their molecular complexes, J. Am. Chem. Soc., 1924, 46, 1504-10. [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]

Kudchadker, Kudchadker, et al., 1979
Kudchadker, Shanti A.; Kudchadker, Arvind P.; Zwolinski, Bruno J., Chemical thermodynamic properties of anthracene and phenanthrene, The Journal of Chemical Thermodynamics, 1979, 11, 11, 1051-1059, https://doi.org/10.1016/0021-9614(79)90135-6 . [all data]

Lenchitz, Velicky, et al., 1971
Lenchitz, C.; Velicky, R.W.; Silvestro, G.; Schlosberg, L.P., Thermodynamic properties of several nitrotoluenes, J. Chem. Thermodyn., 1971, 3, 689-692. [all data]

Edwards, 1950
Edwards, G., The vapour pressure of 2 : 4 : 6-trinitrotoluene, Trans. Faraday Soc., 1950, 46, 423. [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, Yu, Steam Pressures of Nitroaromatic Compouds at Different Temperatures, Zh. Fiz. Khim., 1968, 42, 2921-2925. [all data]

Pella, 1976
Pella, Peter A., Generator for producing trace vapor concentrations of 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and ethylene glycol dinitrate for calibrating explosives vapor detectors, Anal. Chem., 1976, 48, 11, 1632-1637, https://doi.org/10.1021/ac50005a054 . [all data]

Pella, 1977
Pella, Peter A., Measurement of the vapor pressures of tnt, 2,4-dnt, 2,6-dnt, and egdn, The Journal of Chemical Thermodynamics, 1977, 9, 4, 301-305, https://doi.org/10.1016/0021-9614(77)90049-0 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Acree, 1993
Acree, William E., Thermodynamic properties of organic compounds, Thermochimica Acta, 1993, 219, 97-104, https://doi.org/10.1016/0040-6031(93)80486-T . [all data]

Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [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]

Dzidic, Carroll, et al., 1974
Dzidic, I.; Carroll, D.I.; Stillwell, R.N.; Horning, E.C., Gas phase reactions. Ionization by proton transfer to superoxide anions, J. Am. Chem. Soc., 1974, 96, 5258. [all data]

Hobbs and Conde, 1992
Hobbs, J.R.; Conde, E.P., Gas chromatographic retention indices of explosives and nitro-compounds in Advances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem Israel, J. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164. [all data]

Alley and Dykes, 1972
Alley, B.J.; Dykes, H.W.H., Gas-Liquid Chromatographic Determination of Nitrate Esters,Stabilizers and Plasticizers in Nitrocellulose-Base Propellants, J. Chromatogr., 1972, 71, 1, 23-37, https://doi.org/10.1016/S0021-9673(01)85687-9 . [all data]

Staples, 2005
Staples, E.J., Ultrahigh-speed chromatography and virtual chemical sensors for detecting explosives and chemical warfare agents, IEEE Sens. J., 2005, 5, 4, 622-631, https://doi.org/10.1109/JSEN.2005.850990 . [all data]

Staples, 2004
Staples, E.J., Analysis of odors from explosives using an electronic nose, 2004, retrieved from http://www.estcal.com/TechPapers/Odors_of_Explosives.doc. [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, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy 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
  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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