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
View 3d structure (requires JavaScript / HTML 5) - Other names: Benzene, 1,1',1''-methylidynetris-; Methane, triphenyl-; Tritane; Benzene,1,1',1"-methylidynetris-; 1,1',1''-Methylidynetris[benzene]
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Condensed phase thermochemistry data
Go To: Top, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
DH - Eugene S. Domalski and Elizabeth D. Hearing
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 40.08 ± 0.98 | 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 |
ΔfH°solid | 38.94 ± 0.96 | kcal/mol | Ccb | Parks, West, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = 38.71 ± 0.02 kcal/mol; ALS |
ΔfH°solid | Ccb | Schmidlin, 1906 | uncertain value: 34.6 kcal/mol; Undetermine error; ALS | ||
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2374.40 ± 0.30 | kcal/mol | Ccb | Coops, Mulder, et al., 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2370.17 ± 0.32 kcal/mol; See Coops, Mulder, et al., 1946; Corresponding ΔfHºsolid = 40.91 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2372.43 ± 0.95 | kcal/mol | Ccb | Parks, West, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2372.23 ± 0.95 kcal/mol; Corresponding ΔfHºsolid = 38.94 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | Ccb | Schmidlin, 1906 | uncertain value: -2385.1 kcal/mol; Undetermine error; ALS | ||
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 74.59 | cal/mol*K | N/A | Huffman, Parks, et al., 1930 | Extrapolation below 90 K, 99.75 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
108.5 | 373. | Kurbatov, 1950 | T = 100 to 343°C.; DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
70.65 | 298.15 | Steele, 1979 | DH |
79.71 | 298.1 | Eibert, 1944 | T = 30 to 200°C, equations only, in t°C. Cp(c) = 0.326 cal/g*K (30 to 90°C); Cp(liq) = 0.325 + 0.000889t cal/g*K (92 to 200°C).; DH |
73.80 | 303. | Spaght, Thomas, et al., 1932 | T = 30 to 110°C.; DH |
70.60 | 298.15 | Smith and Andrews, 1931 | T = 102 to 346 K. Value is unsmoothed experimental datum.; DH |
70.41 | 294.3 | Huffman, Parks, et al., 1930 | T = 89 to 294 K. Value is unsmoothed datum.; DH |
62.40 | 298.15 | Hildebrand, Duschak, et al., 1917 | T = 293 to 418 K. From heat content data.; DH |
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. |
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Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, IR Spectrum, UV/Visible spectrum, 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 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, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 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) |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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
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, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]
Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A.,
Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols,
J. Am. Chem. Soc., 1946, 68, 2524-2527. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Schmidlin, 1906
Schmidlin, M.J.,
Recherches chimiques et thermochimiques sur la constitution des rosanilines,
Ann. Chim. Phys., 1906, 1, 195-256. [all data]
Coops, Mulder, et al., 1947
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
Researches on heat of combustion IV. Technique for the determination of the heats of combustion of volatile liquids,
Recl. Trav. Chim. Pays-Bas, 1947, 66, 153-160. [all data]
Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
The heats of combustion of a number of hydrocarbons,
Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [all data]
Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C.,
Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons,
J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]
Kurbatov, 1950
Kurbatov, V.Ya.,
Specific heats of liquids. III. Specific heat of hydrocarbons with several noncondensed rings,
Zhur. Obshch. Khim., 1950, 20, 1139-1144. [all data]
Steele, 1979
Steele, W.V.,
The standard enthalpies of formation of the triphenyl compounds of the group V elements. 2. Triphenylbismuth and the Ph-Bi mean bond-dissociation energy,
J. Chem. Thermodynam., 1979, 11, 187-192. [all data]
Eibert, 1944
Eibert, J.,
Thesis Washington University (St. Louis), 1944. [all data]
Spaght, Thomas, et al., 1932
Spaght, M.E.; Thomas, S.B.; Parks, G.S.,
Some heat capacity data on organic compounds obtained with a radiation calorimeter,
J. Phys. Chem., 1932, 36, 882-888. [all data]
Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H.,
Thermal energy studies. I. Phenyl derivatives of methane,
ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]
Hildebrand, Duschak, et al., 1917
Hildebrand, J.H.; Duschak, A.D.; Foster, A.H.,
and Beebe, C.W. The specific heats and heats of fusion of triphenylmethane, anthraquinone and anthracene,
J. Am. Chem. Soc., 1917, 39, 2293-2297. [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, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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