Triphenylmethane
- Formula: C19H16
- Molecular weight: 244.3303
- IUPAC Standard InChI: InChI=1S/C19H16/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
- 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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Reaction thermochemistry data
Go To: Top, 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
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 |
+
= 2
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, Reaction thermochemistry 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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature 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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