Triphenylmethane

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Reaction thermochemistry 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:
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
Δr358.7 ± 2.2kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr360.8 ± 2.5kcal/molG+TSBartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr350.7 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr352.8 ± 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
Δr-40.5 ± 0.6kcal/molChydBent and Cuthbertson, 1936liquid phase; ALS
Δr-34.8kcal/molChydBent and Cuthbertson, 1936liquid phase; solvent: Ethylacetate; ALS

Chlorine anion + Triphenylmethane = (Chlorine anion • Triphenylmethane)

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

Quantity Value Units Method Reference Comment
Δr4.10kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (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
Δr-55.21 ± 0.53kcal/molRSCHolm, 1981solvent: Diethyl ether; MS

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
8.34 ± 0.03PIRodionov, Potapov, et al., 1973LLK
8.34 ± 0.04PIPotapov, Kardash, et al., 1972LLK
8.40 ± 0.05PEDistefano, Pignataro, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C13H11+10.9C6H5PIRodionov, Potapov, et al., 1973LLK

De-protonation reactions

C19H15- + Hydrogen cation = Triphenylmethane

By formula: C19H15- + H+ = C19H16

Quantity Value Units Method Reference Comment
Δr358.7 ± 2.2kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr360.8 ± 2.5kcal/molG+TSBartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr350.7 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr352.8 ± 2.3kcal/molIMREBartmessgas phase; value altered from reference due to change in acidity scale; B

References

Go To: Top, Reaction thermochemistry 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.

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]

Rodionov, Potapov, et al., 1973
Rodionov, A.N.; Potapov, V.K.; Rogozhin, K.L., Photoionization of certain aromatic heteroorganic compounds, High Energy Chem., 1973, 7, 249, In original 278. [all data]

Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [all data]

Distefano, Pignataro, et al., 1976
Distefano, G.; Pignataro, S.; Szepes, L.; Borossay, J., Photoelectron spectroscopy study of the triphenyl derivatives of the group IV elements, J. Organomet. Chem., 1976, 104, 173. [all data]


Notes

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