Diphenylmethane
- Formula: C13H12
- Molecular weight: 168.2344
- IUPAC Standard InChIKey: CZZYITDELCSZES-UHFFFAOYSA-N
- CAS Registry Number: 101-81-5
- 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'-methylenebis-; Methane, diphenyl-; Benzene, (phenylmethyl)-; Benzylbenzene; Ditan; Ditane; Benzene, benzyl-; Toluene, α-phenyl-; 1,1'-Dimethylenebis(benzene); NSC 4708
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Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 535. ± 4. | K | AVG | N/A | Average of 51 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 299. ± 2. | K | AVG | N/A | Average of 83 out of 85 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 780. ± 60. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 27. ± 3. | bar | N/A | Tsonopoulos and Ambrose, 1995 | |
Pc | 27.10 | bar | N/A | Wieczorek and Kobayashi, 1980 | Uncertainty assigned by TRC = 3.00 bar; TRC |
Pc | 59.7817 | bar | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 3.0398 bar; TRC |
Pc | 28.5736 | bar | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 1.0132 bar; TRC |
Pc | 28.5736 | bar | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 1.0132 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.563 | l/mol | N/A | Tsonopoulos and Ambrose, 1995 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 1.8 ± 0.3 | mol/l | N/A | Tsonopoulos and Ambrose, 1995 | |
ρc | 1.780 | mol/l | N/A | Stephenson, 1992 | Uncertainty assigned by TRC = 0.12 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 65. ± 10. | kJ/mol | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 87.2 ± 0.7 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient high-quality literature values to make a good evaluation with a high degree of confidence. In general, the evaluated uncertainty limits are on the order of (0.5 to 2.5) kJ/mol.; DRB |
ΔsubH° | 87.6 ± 0.8 | kJ/mol | N/A | Verevkin, 1999 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
64.1 ± 0.1 | 340. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
61.0 ± 0.1 | 380. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
57.9 ± 0.1 | 420. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
55.0 ± 0.1 | 460. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
52.0 ± 0.2 | 500. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
48.9 ± 0.3 | 540. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
66.4 ± 0.5 | 323. | GS | Verevkin, 1999 | Based on data from 303. to 343. K.; AC |
61.8 | 368. | N/A | Sohda, Okazaki, et al., 1990 | Based on data from 353. to 433. K.; AC |
63.7 | 363. | N/A | Sasse, N'guimbi, et al., 1989 | Based on data from 303. to 402. K.; AC |
72.2 | 310. | A | Stephenson and Malanowski, 1987 | Based on data from 295. to 383. K.; AC |
56.7 | 438. | A | Stephenson and Malanowski, 1987 | Based on data from 423. to 583. K.; AC |
55.8 | 445. | N/A | Wieczorek and Kobayashi, 1981 | AC |
49.0 | 535. | N/A | Wieczorek and Kobayashi, 1981 | AC |
54.2 | 505. | N/A | Crafts, 1915 | Based on data from 490. to 555. K. See also Boublik, Fried, et al., 1984.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
88.5 ± 0.8 | 284. | GS | Verevkin, 1999 | Based on data from 273. to 295. K.; AC |
71.5 | 286. | EM | Sasse, N'guimbi, et al., 1989 | Based on data from 273. to 298. K.; AC |
83.3 ± 3.3 | 286. | HSA | Chickos, Annunziata, et al., 1986 | Based on data from 276. to 295. K.; AC |
82.47 ± 0.63 | 299.8 | V | Aihara, 1959 | crystal phase; ALS |
64.0 | 278. to 299. | N/A | Bloink, Pausacker, et al., 1951 | See also Jones, 1960.; AC |
72.0 ± 0.8 | 297. | N/A | Wolf and Weghofer, 1938 | AC |
72.0 ± 0.8 | 297. | V | Wolf and Weghofer, 1938, 2 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.01 | 298.4 | N/A | Chirico and Steele, 2005 | AC |
18.58 | 298.3 | AC | Domalski and Hearing, 1996 | AC |
18.569 | 298.3 | N/A | Huffman, Parks, et al., 1930 | DH |
19.050 | 299.4 | N/A | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
62.34 | 298.3 | Domalski and Hearing, 1996 | CAL |
62.25 | 298.3 | Huffman, Parks, et al., 1930 | DH |
Gas phase ion energetics data
Go To: Top, Phase change 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 802.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 769.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
<0.156 ± 0.043 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.3 eV, anion unbound.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.4 | EI | Terlouw, Heerma, et al., 1974 | LLK |
8.7 ± 0.1 | EI | Bohlmann, Koppel, et al., 1974 | LLK |
8.55 ± 0.03 | PI | Potapov, Kardash, et al., 1972 | LLK |
9.00 ± 0.05 | EI | Pignataro, Mancini, et al., 1972 | LLK |
8.67 ± 0.05 | PE | Distefano, Pignataro, et al., 1976 | Vertical value; LLK |
8.8 | PE | Eaton and Traylor, 1974 | Vertical value; LLK |
8.80 ± 0.02 | PE | Maier and Turner, 1973 | Vertical value; LLK |
9.1 | PE | Pignataro, Mancini, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H7+ | 11.5 ± 0.1 | C6H5 | EI | Innorta, Torroni, et al., 1973 | LLK |
C13H9+ | 14.9 ± 0.1 | H2+H | EI | Rapp, Staab, et al., 1970 | RDSH |
C13H11+ | 11.2 ± 0.1 | H | EI | Bohlmann, Koppel, et al., 1974 | LLK |
De-protonation reactions
C13H11- + =
By formula: C13H11- + H+ = C13H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1521. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1512. ± 9.6 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1499. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1489. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
Gas Chromatography
Go To: Top, Phase change 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 |
---|---|---|---|---|---|
Capillary | OV-1 | 200. | 1448.7 | Giumanini, Verardo, et al., 2001 | |
Capillary | SE-30 | 100. | 1414.6 | Tudor, 1997 | 40. m/0.35 mm/0.35 μm |
Capillary | DB-1 | 160.00 | 1423.5 | van Haelst, van der Wielen, et al., 1996 | 30. m/0.32 mm/0.25 μm, He |
Capillary | DB-1 | 170.00 | 1429.8 | van Haelst, van der Wielen, et al., 1996 | 30. m/0.32 mm/0.25 μm, He |
Capillary | OV-101 | 140. | 1412.4 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | OV-101 | 160. | 1429.4 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
Packed | SE-30 | 150. | 1415. | Shlyakhov, Anvaer, et al., 1975 | |
Packed | SE-30 | 200. | 1449. | Shlyakhov, Anvaer, et al., 1975 | |
Packed | Apiezon L | 150. | 1458. | Shlyakhov, Anvaer, et al., 1975 |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1980. | Toda, Mihara, et al., 1983 | 2. K/min; Column length: 50. m; Column diameter: 0.23 mm; Tstart: 80. C; Tend: 200. C |
Capillary | Carbowax 20M | 1984. | Toda, Mihara, et al., 1983 | 2. K/min; Column length: 50. m; Column diameter: 0.23 mm; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 1405.2 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
Capillary | SE-54 | 1418.1 | Shapi and Hesso, 1990 | 25. m/0.32 mm/0.15 μm, He, 40. C @ 1. min, 5. K/min, 280. C @ 15. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP-Sil5 CB MS | 1403.9 | Helmig, Bocquet, et al., 2004 | 60. m/0.32 mm/0.25 μm, He; Program: 40C(1min) => 25C/min => 120C => 2C/min => 190C => 25C/min => 250C (5min) |
Capillary | DB-1 | 1380.1 | Helmig, Bocquet, et al., 2004 | 30. m/0.32 mm/0.1 μm, He; Program: 40C(5min) => 20C/min => 100C => 2C/min => 160C => 40C/min => 250C (5min) |
Capillary | DB-1 | 1389.6 | Helmig, Bocquet, et al., 2004 | 30. m/0.32 mm/0.25 μm, He; Program: 40C(5min) => 20C/min => 100C => 2C/min => 160C => 40C/min => 250C (5min) |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 120. | 1412. | Nabivach and Gerasimenko, 1996 | |
Capillary | Polidimethyl siloxane | 130. | 1401. | Nabivach and Gerasimenko, 1996 | |
Capillary | Polidimethyl siloxane | 130. | 1406. | Nabivach and Gerasimenko, 1996 |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 1400. | Elizalde-González, Hutfliess, et al., 1996 | 50. m/0.2 mm/0.33 μm, H2, 3. K/min, 300. C @ 35. min; Tstart: 60. C |
Capillary | Ultra-1 | 1393. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-1 | 1424. | Grigor'ev, Bozhko, et al., 2009 | Helium; Program: not specified |
Capillary | DB-1 | 1380.1 | Helmig, Revermann, et al., 2003 | 30. m/0.32 mm/0.1 μm, He; Program: 40C (2min) => 20C/min => 80C => 3C/min => 145C => 45C/min => 225C (3min) |
Capillary | DB-1 | 1416. | Peng, 1996 | 30. m/0.53 mm/1.5 μm; Program: 40 0C (4 min) 8 0C/min -> 200 0C (1 min) 5 0C/min -> 280 0C (20 min) |
Capillary | Methyl Silicone | 1403. | Zenkevich, 1994 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1461. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1994. | Peng, 1996 | 30. m/0.53 mm/1.0 μm; Program: 40 0C (4 min) 4 0C/min -> 200 0C (20 min) |
Capillary | DB-Wax | 1994. | Peng, Yang, et al., 1991 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 247.0 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | HP-5 | 241.6 | Shao, Wang, et al., 2006 | 30. m/0.3 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | HP-5 | 249.09 | Marynowski, Pieta, et al., 2004 | 60. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 35. C; Tend: 300. C |
Capillary | HP-5 | 249.09 | Marynowski, Pieta, et al., 2004 | 60. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 35. C; Tend: 300. C |
Capillary | HP-5 | 245.77 | Piao, Chu, et al., 1999 | 30. m/0.25 mm/0.25 μm, 50. C @ 2. min, 4. K/min, 280. C @ 20. min |
Capillary | BPX-5 | 243.4 | Schwarzbauer, Franke, et al., 1999 | 50. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 3. K/min; Tend: 300. C |
Capillary | CP Sil 8 CB | 245.6 | Bundt, Herbel, et al., 1991 | 50. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 80. C; Tend: 300. C |
Capillary | SE-54 | 245.56 | Guillén, Blanco, et al., 1989 | 20. m/0.22 mm/0.20 μm, He, 4. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | SE-52 | 243.35 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP Sil 8 CB | 245.6 | Bundt, Herbel, et al., 1991 | 50. m/0.25 mm/0.25 μm, He; Program: not specified |
References
Go To: Top, Phase change 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.
Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons,
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Vapor pressure measurements of diphenylmethane, thianaphthene, and bicyclohexyl at elevated temperatures,
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Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen,
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Measurement of Critical Constants,
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Tension de vapeur d'hydrocarbures polyaromatiques dans le domaine 10-3--10 Torr,
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Vapor-pressure measurements of 1-methylnaphthalene, 2-methylnaphthalene, and 9,10-dihydrophenanthrene at elevated temperatures,
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The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
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Uber sublimationswarmen,
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Notes
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- Symbols used in this document:
AE Appearance energy EA Electron affinity Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Vc Critical volume ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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