Triphenylmethane
- Formula: C19H16
- Molecular weight: 244.3303
- IUPAC Standard InChIKey: AAAQKTZKLRYKHR-UHFFFAOYSA-N
- CAS Registry Number: 519-73-3
- 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: Benzene, 1,1',1''-methylidynetris-; Methane, triphenyl-; Tritane; Benzene,1,1',1"-methylidynetris-; 1,1',1''-Methylidynetris[benzene]
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Gas phase 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:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 276.1 ± 5.0 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 541. | J/mol*K | N/A | Marcus Y., 1986 | This value calculated from published spectroscopic and structural data is in close agreement with estimations by a method of increments (549-568 J/mol*K [85MAR/LOE, Dorofeeva O.V., 1997]). Value obtained from calorimetric data (722.7 J/mol*K [85MAR/LOE]) authors do not regard as reliable.; GT |
Condensed phase 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:
DH - Eugene S. Domalski and Elizabeth D. Hearing
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 167.7 ± 4.1 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB |
ΔfH°solid | 162.9 ± 4.0 | kJ/mol | Ccb | Parks, West, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = 162.0 ± 0.08 kJ/mol; ALS |
ΔfH°solid | Ccb | Schmidlin, 1906 | uncertain value: 145. kJ/mol; Undetermine error; ALS | ||
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -9934.5 ± 1.3 | kJ/mol | Ccb | Coops, Mulder, et al., 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -9916.8 ± 1.3 kJ/mol; See Coops, Mulder, et al., 1946; Corresponding ΔfHºsolid = 171.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -9926.2 ± 4.0 | kJ/mol | Ccb | Parks, West, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = -9925.4 ± 4.0 kJ/mol; Corresponding ΔfHºsolid = 162.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | Ccb | Schmidlin, 1906 | uncertain value: -9979.3 kJ/mol; Undetermine error; ALS | ||
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 312.1 | J/mol*K | N/A | Huffman, Parks, et al., 1930 | Extrapolation below 90 K, 99.75 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
454.0 | 373. | Kurbatov, 1950 | T = 100 to 343°C.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
295.6 | 298.15 | Steele, 1979 | DH |
333.5 | 298.1 | Eibert, 1944 | T = 30 to 200°C, equations only, in t°C. Cp(c) = 0.326 cal/g*K (30 to 90°C); Cp(liq) = 0.325 + 0.000889t cal/g*K (92 to 200°C).; DH |
308.8 | 303. | Spaght, Thomas, et al., 1932 | T = 30 to 110°C.; DH |
295.4 | 298.15 | Smith and Andrews, 1931 | T = 102 to 346 K. Value is unsmoothed experimental datum.; DH |
294.6 | 294.3 | Huffman, Parks, et al., 1930 | T = 89 to 294 K. Value is unsmoothed datum.; DH |
261.1 | 298.15 | Hildebrand, Duschak, et al., 1917 | T = 293 to 418 K. From heat content data.; 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
MS - José A. Martinho Simões
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
C19H15- + =
By formula: C19H15- + H+ = C19H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1501. ± 9.2 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 1510. ± 10. | kJ/mol | G+TS | Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1467. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 1476. ± 9.6 | kJ/mol | IMRE | Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
By formula: H2 + C38H30 = 2C19H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -169. ± 3. | kJ/mol | Chyd | Bent and Cuthbertson, 1936 | liquid phase; ALS |
ΔrH° | -146. | kJ/mol | Chyd | Bent and Cuthbertson, 1936 | liquid phase; solvent: Ethylacetate; ALS |
By formula: Cl- + C19H16 = (Cl- • C19H16)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 17.2 | kJ/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
17. | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
C19H15BrMg (solution) + (g) =
(solution) + Br2Mg (solution)
By formula: C19H15BrMg (solution) + HBr (g) = C19H16 (solution) + Br2Mg (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -231.0 ± 2.2 | kJ/mol | RSC | Holm, 1981 | solvent: Diethyl ether; MS |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y.,
Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons,
J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]
Marcus Y., 1986
Marcus Y.,
Entropies of tetrahedral M-phenyl species,
J. Chem. Soc., Faraday Trans. 1, 1986, 82, 993-1006. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A.,
Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols,
J. Am. Chem. Soc., 1946, 68, 2524-2527. [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]
Schmidlin, 1906
Schmidlin, M.J.,
Recherches chimiques et thermochimiques sur la constitution des rosanilines,
Ann. Chim. Phys., 1906, 1, 195-256. [all data]
Coops, Mulder, et al., 1947
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
Researches on heat of combustion IV. Technique for the determination of the heats of combustion of volatile liquids,
Recl. Trav. Chim. Pays-Bas, 1947, 66, 153-160. [all data]
Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
The heats of combustion of a number of hydrocarbons,
Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [all data]
Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C.,
Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons,
J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]
Kurbatov, 1950
Kurbatov, V.Ya.,
Specific heats of liquids. III. Specific heat of hydrocarbons with several noncondensed rings,
Zhur. Obshch. Khim., 1950, 20, 1139-1144. [all data]
Steele, 1979
Steele, W.V.,
The standard enthalpies of formation of the triphenyl compounds of the group V elements. 2. Triphenylbismuth and the Ph-Bi mean bond-dissociation energy,
J. Chem. Thermodynam., 1979, 11, 187-192. [all data]
Eibert, 1944
Eibert, J.,
Thesis Washington University (St. Louis), 1944. [all data]
Spaght, Thomas, et al., 1932
Spaght, M.E.; Thomas, S.B.; Parks, G.S.,
Some heat capacity data on organic compounds obtained with a radiation calorimeter,
J. Phys. Chem., 1932, 36, 882-888. [all data]
Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H.,
Thermal energy studies. I. Phenyl derivatives of methane,
ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]
Hildebrand, Duschak, et al., 1917
Hildebrand, J.H.; Duschak, A.D.; Foster, A.H.,
and Beebe, C.W. The specific heats and heats of fusion of triphenylmethane, anthraquinone and anthracene,
J. Am. Chem. Soc., 1917, 39, 2293-2297. [all data]
Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G.,
Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase,
Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005
. [all data]
Bartmess
Bartmess, J.E.,
The Gas Phase Thermochemistry of Ph3C-, Ph3C., and Ph3C+, 32nd Ann. Conf. on Mass Spectrom. Allied Topics, San Antonio TX 27 May-1 June 1984. Abstracts p. 472. [all data]
Bent and Cuthbertson, 1936
Bent, H.E.; Cuthbertson, G.R.,
Single bond energies. II. The C-C bond in hexaphenylethane,
J. Am. Chem. Soc., 1936, 58, 170-173. [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]
Holm, 1981
Holm, T.,
J. Chem. Soc., Perkin Trans. II, 1981, 464.. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°gas Entropy of gas at standard conditions S°solid,1 bar Entropy of solid at standard conditions (1 bar) T Temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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