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Triphenylmethane

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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
Deltafgas276.1 ± 5.0kJ/molReviewRoux, Temprado, et al., 2008There 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
gas541.J/mol*KN/AMarcus Y., 1986This 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
Deltafsolid167.7 ± 4.1kJ/molReviewRoux, Temprado, et al., 2008There 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
Deltafsolid162.9 ± 4.0kJ/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = 162.0 ± 0.08 kJ/mol; ALS
Deltafsolid  CcbSchmidlin, 1906uncertain value: 145. kJ/mol; Undetermine error; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-9934.5 ± 1.3kJ/molCcbCoops, Mulder, et al., 1947Reanalyzed by Cox and Pilcher, 1970, Original value = -9916.8 ± 1.3 kJ/mol; See Coops, Mulder, et al., 1946; Corresponding «DELTA»fsolid = 171.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-9926.2 ± 4.0kJ/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -9925.4 ± 4.0 kJ/mol; Corresponding «DELTA»fsolid = 162.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid  CcbSchmidlin, 1906uncertain value: -9979.3 kJ/mol; Undetermine error; ALS
Quantity Value Units Method Reference Comment
solid,1 bar312.1J/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 99.75 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
454.0373.Kurbatov, 1950T = 100 to 343°C.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
295.6298.15Steele, 1979DH
333.5298.1Eibert, 1944T = 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
308.8303.Spaght, Thomas, et al., 1932T = 30 to 110°C.; DH
295.4298.15Smith and Andrews, 1931T = 102 to 346 K. Value is unsmoothed experimental datum.; DH
294.6294.3Huffman, Parks, et al., 1930T = 89 to 294 K. Value is unsmoothed datum.; DH
261.1298.15Hildebrand, Duschak, et al., 1917T = 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- + Hydrogen cation = Triphenylmethane

By formula: C19H15- + H+ = C19H16

Quantity Value Units Method Reference Comment
Deltar1501. ± 9.2kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Deltar1510. ± 10.kJ/molG+TSBartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1467. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B
Deltar1476. ± 9.6kJ/molIMREBartmessgas phase; value altered from reference due to change in acidity scale; B

Hydrogen + Benzene, 1,1',1'',1''',1'''',1'''''-(1,2-ethanediylidyne)hexakis- = 2Triphenylmethane

By formula: H2 + C38H30 = 2C19H16

Quantity Value Units Method Reference Comment
Deltar-169. ± 3.kJ/molChydBent and Cuthbertson, 1936liquid phase; ALS
Deltar-146.kJ/molChydBent and Cuthbertson, 1936liquid phase; solvent: Ethylacetate; ALS

Chlorine anion + Triphenylmethane = (Chlorine anion bullet Triphenylmethane)

By formula: Cl- + C19H16 = (Cl- bullet C19H16)

Quantity Value Units Method Reference Comment
Deltar17.2kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
17.300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

C19H15BrMg (solution) + Hydrogen bromide (g) = Triphenylmethane (solution) + Br2Mg (solution)

By formula: C19H15BrMg (solution) + HBr (g) = C19H16 (solution) + Br2Mg (solution)

Quantity Value Units Method Reference Comment
Deltar-231.0 ± 2.2kJ/molRSCHolm, 1981solvent: 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

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