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]
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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 |
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 |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Gas Chromatography, 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 ± 0.03 | PI | Rodionov, Potapov, et al., 1973 | LLK |
8.34 ± 0.04 | PI | Potapov, Kardash, et al., 1972 | LLK |
8.40 ± 0.05 | PE | Distefano, Pignataro, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C13H11+ | 10.9 | C6H5 | PI | Rodionov, Potapov, et al., 1973 | LLK |
De-protonation 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 |
Gas Chromatography
Go To: Top, Reaction thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SE-30 | 200. | 1978. | Shlyakhov, Anvaer, et al., 1975 |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1982. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1997. | Xie, Sun, et al., 2008 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (2 min) 4 0C/min -> 220 0C 20 0C/min -> 280 0C |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BPX-5 | 327.8 | Schwarzbauer, Franke, et al., 1999 | 50. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 3. K/min; Tend: 300. C |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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]
Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I.,
On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices,
Zh. Anal. Khim., 1975, 30, 788-792. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Xie, Sun, et al., 2008
Xie, J.; Sun, B.; Zheng, F.; Wang, S.,
Volatile flavor constituents in roasted pork of mini-pig,
Food Chem., 2008, 109, 3, 506-514, https://doi.org/10.1016/j.foodchem.2007.12.074
. [all data]
Schwarzbauer, Franke, et al., 1999
Schwarzbauer, J.; Franke, S.; Francke, W.,
Chlorinated di- and triphenylmethanes in sediments of the Mulde and Elbe rivers. Part IV of organic compounds as contaminants of the Elbe river and its tributaries,
Fresenius J. Anal. Chem., 1999, 365, 6, 529-536, https://doi.org/10.1007/s002160051517
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.