Mesitylene
- Formula: C9H12
- Molecular weight: 120.1916
- IUPAC Standard InChIKey: AUHZEENZYGFFBQ-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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)
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Phase change data
Go To: Top, 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 437.8 ± 0.8 | K | AVG | N/A | Average of 48 out of 54 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 225. ± 8. | K | AVG | N/A | Average of 21 out of 22 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 228.42 | K | N/A | Taylor and Kilpatrick, 1955 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 639. ± 4. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 31.3 ± 0.4 | bar | N/A | Tsonopoulos and Ambrose, 1995 | |
Pc | 31.619 | bar | N/A | Kay and Pak, 1980 | Uncertainty assigned by TRC = 0.0031 bar; Visual, Table 2, mercury interface at room temperature.; TRC |
Pc | 32.55 | bar | N/A | Kay and Pak, 1980 | Uncertainty assigned by TRC = 0.0032 bar; Visual, Table 2, mercury interface at sample tempera; TRC |
Pc | 31.27 | bar | N/A | Ambrose, Broderick, et al., 1967 | Uncertainty assigned by TRC = 0.06 bar; TRC |
Pc | 32.60 | bar | N/A | Altschul, 1893 | Uncertainty assigned by TRC = 0.0981 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 47.51 ± 0.07 | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
46.2 ± 1.3 | 319. | MM | Wiberg and Waldron, 1991 | Based on data from 296. to 342. K.; AC |
43.5 | 363. | N/A | Park and Gmehling, 1989 | Based on data from 348. to 424. K.; AC |
49.7 | 264. | A | Stephenson and Malanowski, 1987 | Based on data from 249. to 356. K.; AC |
43.9 | 369. | A | Stephenson and Malanowski, 1987 | Based on data from 354. to 445. K. See also Forziati, Norris, et al., 1949.; AC |
47.7 | 286. | MM | Chickos, Hyman, et al., 1981 | Based on data from 273. to 299. K.; AC |
51.1 | 262. | RG | Hopke and Sears, 1948 | Based on data from 255. to 268. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
354.64 to 438.87 | 4.19927 | 1569.622 | -63.572 | Forziati, Norris, et al., 1949, 2 |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.51 | 228.4 | Domalski and Hearing, 1996 | See also Radomska and Radomski, 1991.; AC |
9.51 | 228.4 | Radomska and Radomski, 1991 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
9.5148 | 228.42 | crystaline, I | liquid | Taylor and Kilpatrick, 1955, 2 | Metastable melting points at 221.46 K and 223.35 K.; DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
41.65 | 228.42 | crystaline, I | liquid | Taylor and Kilpatrick, 1955, 2 | Metastable; DH |
Gas phase ion energetics data
Go To: Top, 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:
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.40 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 836.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 808.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
835.1 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
808.8 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.41 ± 0.01 | EQ | Lias and Ausloos, 1978 | LLK |
8.46 | CTS | Kobayashi, Kobayashi, et al., 1973 | LLK |
8.2 ± 0.1 | EI | Gilbert, Leach, et al., 1973 | LLK |
8.47 | CTS | Huttner and Fischer, 1967 | RDSH |
8.40 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.55 | CTS | Kinoshita, 1962 | RDSH |
8.39 ± 0.01 | PI | Price, Bralsford, et al., 1959 | RDSH |
8.41 ± 0.02 | PI | Vilesov and Terenin, 1957 | RDSH |
8.42 | PE | Howell, Goncalves, et al., 1984 | Vertical value; LBLHLM |
8.42 | PE | Cetinkaya, Lappert, et al., 1983 | Vertical value; LBLHLM |
8.45 | PE | Worley and Webb, 1980 | Vertical value; LLK |
8.45 ± 0.05 | PE | Gower, Kane-Maguire, et al., 1977 | Vertical value; LLK |
8.45 ± 0.05 | PE | Evans, Green, et al., 1974 | Vertical value; LLK |
8.65 ± 0.03 | PE | Klessinger, 1972 | Vertical value; LLK |
References
Go To: Top, 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.
Taylor and Kilpatrick, 1955
Taylor, R.D.; Kilpatrick, J.E.,
Entropy, Heat Capacity and Heats of Trans. of 1,3,5-Trimethylbenzene,
J. Chem. Phys., 1955, 23, 1232-5. [all data]
Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons,
J. Chem. Eng. Data, 1995, 40, 547-558. [all data]
Kay and Pak, 1980
Kay, W.B.; Pak, S.C.,
Determination of the critical constants of high-boiling hydrocarbons. Experiments with gallium as a containing fluid,
J. Chem. Thermodyn., 1980, 12, 673. [all data]
Ambrose, Broderick, et al., 1967
Ambrose, D.; Broderick, B.E.; Townsend, R.,
The Vapour Pressures above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons,
J. Chem. Soc. , 1967, 1967, 1967, 633-41. [all data]
Altschul, 1893
Altschul, M.,
The critical values of some organic compounds,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1893, 11, 577. [all data]
Wiberg and Waldron, 1991
Wiberg, K.B.; Waldron, R.F.,
Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. strain energies and conformations,
J. Am. Chem. Soc., 1991, 113, 7697-7705. [all data]
Park and Gmehling, 1989
Park, So Jin; Gmehling, Juergen,
Isobaric vapor-liquid equilibrium data for the binary systems 1,3,5-trimethylbenzene/N-formylmorpholine and m-xylene/N-formylmorpholine,
J. Chem. Eng. Data, 1989, 34, 4, 399-401, https://doi.org/10.1021/je00058a008
. [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]
Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D.,
Vapor pressures and boiling points of sixty API-NBS hydrocarbons,
J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050
. [all data]
Chickos, Hyman, et al., 1981
Chickos, James S.; Hyman, Arthur S.; Ladon, Liina H.; Liebman, Joel F.,
Measurement and estimation of the heats of vaporization of hydrocarbons,
J. Org. Chem., 1981, 46, 21, 4294-4296, https://doi.org/10.1021/jo00334a040
. [all data]
Hopke and Sears, 1948
Hopke, E.R.; Sears, G.W.,
Vapor Pressures of Trimethylbenzenes in the Low Pressure Region 1,2,
J. Am. Chem. Soc., 1948, 70, 11, 3801-3803, https://doi.org/10.1021/ja01191a077
. [all data]
Forziati, Norris, et al., 1949, 2
Forziati, A.F.; Norris, W.R.; Rossini, F.D.,
Vapor Pressures and Boiling Points of Sixty API-NBS Hydrocarbons,
J. Res. Natl. Bur. Stand. (U.S.), 1949, 43, 6, 555-563, https://doi.org/10.6028/jres.043.050
. [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]
Radomska and Radomski, 1991
Radomska, M.; Radomski, R.,
Phase diagrams in the binary systems of tetracyanoethylene with mesitylene, durene and pentamethylbenzene,
Journal of Thermal Analysis, 1991, 37, 4, 693-704, https://doi.org/10.1007/BF01913148
. [all data]
Taylor and Kilpatrick, 1955, 2
Taylor, R.D.; Kilpatrick, J.E.,
Entropy, heat capacity, heats of transition of 1,3,5-trimethylbenzene,
J. Chem. Phys., 1955, 23, 1232-1235. [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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion 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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