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Triphenylmethane

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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

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Individual Reactions

C19H15- + Hydrogen cation = Triphenylmethane

By formula: C19H15- + H+ = C19H16

Quantity Value Units Method Reference Comment
Deltar358.7 ± 2.2kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Deltar360.8 ± 2.5kcal/molG+TSBartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar350.7 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Deltar352.8 ± 2.3kcal/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-40.5 ± 0.6kcal/molChydBent and Cuthbertson, 1936liquid phase; ALS
Deltar-34.8kcal/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
Deltar4.10kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
4.1300.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-55.21 ± 0.53kcal/molRSCHolm, 1981solvent: Diethyl ether; MS

References

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

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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