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]
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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 |
---|---|---|---|---|---|
ΔfH°gas | 66.0 ± 1.2 | kcal/mol | Review | Roux, Temprado, et al., 2008 | There 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 |
S°gas | 129. | cal/mol*K | N/A | Marcus Y., 1986 | This 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 |
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- + =
By formula: C19H15- + H+ = C19H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 358.7 ± 2.2 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 360.8 ± 2.5 | kcal/mol | G+TS | Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 350.7 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 352.8 ± 2.3 | kcal/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° | -40.5 ± 0.6 | kcal/mol | Chyd | Bent and Cuthbertson, 1936 | liquid phase; ALS |
ΔrH° | -34.8 | kcal/mol | Chyd | Bent and Cuthbertson, 1936 | liquid phase; solvent: Ethylacetate; ALS |
By formula: Cl- + C19H16 = (Cl- • C19H16)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.10 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
4.1 | 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° | -55.21 ± 0.53 | kcal/mol | RSC | Holm, 1981 | solvent: Diethyl ether; MS |
Gas phase ion energetics 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
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° | 358.7 ± 2.2 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 360.8 ± 2.5 | kcal/mol | G+TS | Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 350.7 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 352.8 ± 2.3 | kcal/mol | IMRE | Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Ion clustering 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: Cl- + C19H16 = (Cl- • C19H16)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.10 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
4.1 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
IR Spectrum
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, 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
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-5907 |
NIST MS number | 228265 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | missing citation |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 9007 |
Instrument | Unicam SP 700 |
Melting point | 94 |
Boiling point | 359; 200(10) |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
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
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy S°gas Entropy of gas at standard conditions T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions 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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