Mesitylene

• Formula: C₉H₁₂
• Molecular weight: 120.1916
• IUPAC Standard InChI: InChI=1S/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3 Copy

  
• IUPAC Standard InChIKey: AUHZEENZYGFFBQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-67-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  View 3d structure (requires JavaScript / HTML 5)
• Other names: Benzene, 1,3,5-trimethyl-; s-Trimethylbenzene; 1,3,5-Trimethylbenzene; sym-Trimethylbenzene; Fleet-X; TMB; UN 2325; 2,4,6-Trimethylbenzene; 3,5-Dimethyltoluene; NSC 9273; Trimethylbenzene; Trimethylbenzol; 1,3,5-trimethylbenzene (mesitylene); Trimethylbenzene (Related); Trimethylbenzol (Related)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Reaction thermochemistry data

Go To: Top, Henry's Law data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
RCD - Robert C. Dunbar

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

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₉H₁₂ = (C₃H₉Si⁺ • C₉H₁₂)

Free energy of reaction

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₉H₁₂ = (C₃H₉Sn⁺ • C₉H₁₂)

Free energy of reaction

C₉H₁₃⁺ +  = (C₉H₁₃⁺ • )

By formula: C₉H₁₃⁺ + C₉H₁₂ = (C₉H₁₃⁺ • C₉H₁₂)

Free energy of reaction

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + C₉H₁₂ = (C₁₁H₁₀⁺ • C₉H₁₂)

Bond type: Charge transfer bond (positive ion)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₉H₁₂ = (C₆H₇N⁺ • C₉H₁₂)

Bond type: Charge transfer bond (positive ion)

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₉H₁₂ = (C₉H₁₂⁺ • C₉H₁₂)

Bond type: Charge transfer bond (positive ion)

 + 3 =

By formula: C₉H₁₂ + 3H₂ = C₉H₁₈

 +  = ( • )

By formula: Cl^- + C₉H₁₂ = (Cl^- • C₉H₁₂)

Free energy of reaction

 +  = ( • )

By formula: H₄N⁺ + C₉H₁₂ = (H₄N⁺ • C₉H₁₂)

2 + 6 =  + 

By formula: 2C₉H₁₂ + 6H₂ = C₉H₁₈ + C₉H₁₈

( • ) +  = ( • 2)

By formula: (Cr⁺ • C₉H₁₂) + C₉H₁₂ = (Cr⁺ • 2C₉H₁₂)

 +  = ( • )

By formula: Cr⁺ + C₉H₁₂ = (Cr⁺ • C₉H₁₂)

 +  = ( • )

By formula: Ca⁺ + C₉H₁₂ = (Ca⁺ • C₉H₁₂)

 +  = ( • )

By formula: Sr⁺ + C₉H₁₂ = (Sr⁺ • C₉H₁₂)

Henry's Law data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Henry's Law data, Ion clustering data, UV/Visible spectrum, 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:
MM - Michael M. Meot-Ner (Mautner)
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

View reactions leading to C₉H₁₂⁺ (ion structure unspecified)

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Ion clustering data

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, UV/Visible spectrum, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
B - John E. Bartmess

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

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₉H₁₂ = (C₃H₉Si⁺ • C₉H₁₂)

Free energy of reaction

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₉H₁₂ = (C₃H₉Sn⁺ • C₉H₁₂)

Free energy of reaction

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₉H₁₂ = (C₆H₇N⁺ • C₉H₁₂)

Bond type: Charge transfer bond (positive ion)

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₉H₁₂ = (C₉H₁₂⁺ • C₉H₁₂)

Bond type: Charge transfer bond (positive ion)

C₉H₁₃⁺ +  = (C₉H₁₃⁺ • )

By formula: C₉H₁₃⁺ + C₉H₁₂ = (C₉H₁₃⁺ • C₉H₁₂)

Free energy of reaction

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + C₉H₁₂ = (C₁₁H₁₀⁺ • C₉H₁₂)

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: Ca⁺ + C₉H₁₂ = (Ca⁺ • C₉H₁₂)

 +  = ( • )

By formula: Cl^- + C₉H₁₂ = (Cl^- • C₉H₁₂)

Free energy of reaction

 +  = ( • )

By formula: Cr⁺ + C₉H₁₂ = (Cr⁺ • C₉H₁₂)

( • ) +  = ( • 2)

By formula: (Cr⁺ • C₉H₁₂) + C₉H₁₂ = (Cr⁺ • 2C₉H₁₂)

 +  = ( • )

By formula: H₄N⁺ + C₉H₁₂ = (H₄N⁺ • C₉H₁₂)

 +  = ( • )

By formula: Sr⁺ + C₉H₁₂ = (Sr⁺ • C₉H₁₂)

UV/Visible spectrum

Go To: Top, Reaction thermochemistry data, Henry's Law 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, Notes

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

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH₃)₃Sn⁺ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H., Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies, J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034 . [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [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]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [all data]

Egan and Buss, 1959
Egan, C.J.; Buss, W.C., Determination of the equilibrium constants for the hydrogenation of mesitylene. The thermodynamic properties of the 1,3,5-trimethylcyclohexanes, J. Phys. Chem., 1959, 63, 1887-1889. [all data]

Lin and Dunbar, 1997
Lin, C.-Y.; Dunbar, R.C., Radiative Association Kinetics and Binding Energies of Chromium Ions with Benzene and Benzene Derivatives, Organometallics, 1997, 16, 12, 2691, https://doi.org/10.1021/om960949n . [all data]

Gapeev and Dunbar, 2000
Gapeev, A.; Dunbar, R.C., Binding of Alkaline Earth Halide Ions MX+ to Benzene and Mesitylene, J. Am. Soc. Mass Spectrom., 2000, 13, 5, 477, https://doi.org/10.1016/S1044-0305(02)00373-2 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J., eIonization energies of organic compounds by equilibrium measurements, J. Am. Chem. Soc., 1978, 100, 6027. [all data]

Kobayashi, Kobayashi, et al., 1973
Kobayashi, H.; Kobayashi, M.; Kaizu, Y., Molecular complexes of arenetricarbonylchromium, Bull. Chem. Soc. Jpn., 1973, 46, 3109. [all data]

Gilbert, Leach, et al., 1973
Gilbert, J.R.; Leach, W.P.; Miller, J.R., Ionisation appearance potential measurements in arene chromium tricarbonyls, J. Organomet. Chem., 1973, 49, 219. [all data]

Huttner and Fischer, 1967
Huttner, G.; Fischer, E.O., Uber Aromatenkomplexe von Metallen. XCVIII. Spectroskopische Untersuchungen an Charge-Transfer-Komplexen von Aromaten-Chrom Tricarbonylen mit 1,3,5-Trinitrobenzol, J. Organometal. Chem., 1967, 8, 299. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Price, Bralsford, et al., 1959
Price, W.C.; Bralsford, R.; Harris, P.V.; Ridley, R.G., Ultra-violet spectra and ionization potentials of hydrocarbon molecules, Spectrochim. Acta, 1959, 14, 45. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Howell, Goncalves, et al., 1984
Howell, J.O.; Goncalves, J.M.; Amatore, C.; Klasinc, L.; Wightman, R.M.; Kochi, J.K., Electron transfer from aromatic hydrocarbons and their π-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials, J. Am. Chem. Soc., 1984, 106, 3968. [all data]

Cetinkaya, Lappert, et al., 1983
Cetinkaya, B.; Lappert, M.F.; Suffolk, R.J., Photoelectron spectra of some sterically hindered phenols and related compounds, J. Chem. Res. Synop., 1983, 316. [all data]

Worley and Webb, 1980
Worley, S.D.; Webb, T.R., The electronic structure of transition-metal carbonyl complexes of norbornadiene and mesitylene, J. Organomet. Chem., 1980, 192, 139. [all data]

Gower, Kane-Maguire, et al., 1977
Gower, M.; Kane-Maguire, L.A.P.; Maier, J.P.; Sweigart, D.A., Ultraviolet photoelectron spectra of cyclohepta-1,3,5-triene and mesitylene tricarbonyl complexes of the group 6A metals, J. Chem. Soc. Dalton Trans., 1977, 316. [all data]

Evans, Green, et al., 1974
Evans, S.; Green, J.C.; Jackson, S.E.; Higginson, B., He(I) photoelectron spectra of some transition-metal sandwich complexes, J. Chem. Soc. Dalton Trans., 1974, 304. [all data]

Klessinger, 1972
Klessinger, M., Ionization potentials of substituted benzenes, Angew. Chem. Int. Ed. Engl., 1972, 11, 525. [all data]

Ardyukova, Korobeinicheva, et al., 1973
Ardyukova, T.F.; Korobeinicheva, I.K.; Rezvukhin, A.I., 1,3,5-trimethyl-benzene in Atlas of Spectra of Aromatic and Heterocyclic Substances, V.A. Koptyug, ed(s)., Publishing House "Hauka", Novosibirsk, 1973, 7. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, References

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  T	Temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.