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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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, IR 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 39.4 ± 0.53 | 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°gas | 38.79 ± 0.55 | 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°gas | 39.39 ± 0.38 | kcal/mol | Ccb | Steele, Chirico, et al., 1995 | ALS |
ΔfH°gas | 37.43 | kcal/mol | N/A | Parks and Mosley, 1950 | Value computed using ΔfHliquid° value of 88.9 kj/mol from Parks and Mosley, 1950 and ΔvapH° value of 67.7 kj/mol from Steele, Chirico, et al., 1995.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 104. | 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 (440-451 J/mol*K [85MAR/LOE, Dorofeeva O.V., 1997]). Value obtained from calorimetric data (508.5 J/mol*K [85MAR/LOE]) authors do not regard as reliable. Results of statistical thermodynamics calculation [ Puranik P.G., 1962] are likely to be erroneous (S(300 K)=319 J/mol*K).; GT |
Phase change data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR 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:
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. | atm | N/A | Tsonopoulos and Ambrose, 1995 | |
Pc | 26.75 | atm | N/A | Wieczorek and Kobayashi, 1980 | Uncertainty assigned by TRC = 2.96 atm; TRC |
Pc | 59.0000 | atm | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 3.0000 atm; TRC |
Pc | 28.2000 | atm | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 0.99995 atm; TRC |
Pc | 28.2000 | atm | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 0.99995 atm; 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° | 16. ± 2. | kcal/mol | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 20.8 ± 0.2 | kcal/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° | 20.9 ± 0.2 | kcal/mol | N/A | Verevkin, 1999 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.3 ± 0.02 | 340. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
14.6 ± 0.02 | 380. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
13.8 ± 0.02 | 420. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
13.1 ± 0.02 | 460. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
12.4 ± 0.05 | 500. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
11.7 ± 0.07 | 540. | IP,EB | Chirico and Steele, 2005 | Based on data from 330. to 588. K.; AC |
15.9 ± 0.1 | 323. | GS | Verevkin, 1999 | Based on data from 303. to 343. K.; AC |
14.8 | 368. | N/A | Sohda, Okazaki, et al., 1990 | Based on data from 353. to 433. K.; AC |
15.2 | 363. | N/A | Sasse, N'guimbi, et al., 1989 | Based on data from 303. to 402. K.; AC |
17.3 | 310. | A | Stephenson and Malanowski, 1987 | Based on data from 295. to 383. K.; AC |
13.6 | 438. | A | Stephenson and Malanowski, 1987 | Based on data from 423. to 583. K.; AC |
13.3 | 445. | N/A | Wieczorek and Kobayashi, 1981 | AC |
11.7 | 535. | N/A | Wieczorek and Kobayashi, 1981 | AC |
13.0 | 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 (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.2 ± 0.2 | 284. | GS | Verevkin, 1999 | Based on data from 273. to 295. K.; AC |
17.1 | 286. | EM | Sasse, N'guimbi, et al., 1989 | Based on data from 273. to 298. K.; AC |
19.9 ± 0.79 | 286. | HSA | Chickos, Annunziata, et al., 1986 | Based on data from 276. to 295. K.; AC |
19.71 ± 0.15 | 299.8 | V | Aihara, 1959 | crystal phase; ALS |
15.3 | 278. to 299. | N/A | Bloink, Pausacker, et al., 1951 | See also Jones, 1960.; AC |
17.2 ± 0.2 | 297. | N/A | Wolf and Weghofer, 1938 | AC |
17.2 ± 0.2 | 297. | V | Wolf and Weghofer, 1938, 2 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.543 | 298.4 | N/A | Chirico and Steele, 2005 | AC |
4.441 | 298.3 | AC | Domalski and Hearing, 1996 | AC |
4.4381 | 298.3 | N/A | Huffman, Parks, et al., 1930 | DH |
4.5531 | 299.4 | N/A | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.90 | 298.3 | Domalski and Hearing, 1996 | CAL |
14.88 | 298.3 | Huffman, Parks, et al., 1930 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, Ion clustering data, IR 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 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) | 191.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 183.9 | kcal/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° | 363.6 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 361.3 ± 2.3 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 358.2 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 355.9 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR 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:
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- + C13H12 = (Cl- • C13H12)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 7.40 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
7.4 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
- LIQUID (NEAT) $$ PURITY - ANALYTICAL; PERKIN-ELMER 180 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1300, 2% IN CS2 FOR 1300-650, AND 10% IN CCl4 FOR 650-250 CM-1) VERSUS SOLVENT; Not specified, most likely a grating or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR 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 |
---|---|---|---|---|---|
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, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR 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]
Steele, Chirico, et al., 1995
Steele, W.V.; Chirico, R.D.; Smith, N.K.,
The standard enthalpies of formation of 2-methylbiphenyl and diphenylmethane,
J. Chem. Thermodyn., 1995, 27, 671-678. [all data]
Parks and Mosley, 1950
Parks, G.S.; Mosley, J.R.,
Redetermination of the heat of combustion of diphenylmethane,
J. Am. Chem. Soc., 1950, 72, 1850. [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]
Puranik P.G., 1962
Puranik P.G.,
Vibrational spectra, potential constants, and thermodynamic properties of diphenylmethane,
Proc. Indian Acad. Sci., 1962, A56, 233-238. [all data]
Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons,
J. Chem. Eng. Data, 1995, 40, 547-558. [all data]
Wieczorek and Kobayashi, 1980
Wieczorek, S.A.; Kobayashi, R.,
Vapor pressure measurements of diphenylmethane, thianaphthene, and bicyclohexyl at elevated temperatures,
J. Chem. Eng. Data, 1980, 25, 302. [all data]
Glaser and Ruland, 1957
Glaser, F.; Ruland, H.,
Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen,
Chem. Ing. Techn., 1957, 29, 772. [all data]
Guye and Mallet, 1902
Guye, P.A.; Mallet, E.,
Measurement of Critical Constants,
Arch. Sci. Phys. Nat., 1902, 13, 274-296. [all data]
Stephenson, 1992
Stephenson, R.M.,
Mutual solubilities: water-ketones, water-ethers, and water-gasoline- alcohols,
J. Chem. Eng. Data, 1992, 37, 80-95. [all data]
Verevkin, 1999
Verevkin, Sergey P.,
Thermochemical Properties of Diphenylalkanes,
J. Chem. Eng. Data, 1999, 44, 2, 175-179, https://doi.org/10.1021/je980200e
. [all data]
Chirico and Steele, 2005
Chirico, Robert D.; Steele, William V.,
Thermodynamic Properties of Diphenylmethane «8224»,
J. Chem. Eng. Data, 2005, 50, 3, 1052-1059, https://doi.org/10.1021/je050034s
. [all data]
Sohda, Okazaki, et al., 1990
Sohda, M.; Okazaki, M.; Iwai, Y.; Arai, Y.; Sakoguchi, A.; Ueoka, R.; Kato, Y.,
Vapor pressures of cyclohexylbenzene and diphenylmethane,
The Journal of Chemical Thermodynamics, 1990, 22, 6, 607-608, https://doi.org/10.1016/0021-9614(90)90152-G
. [all data]
Sasse, N'guimbi, et al., 1989
Sasse, K.; N'guimbi, J.; Jose, J.; Merlin, J.C.,
Tension de vapeur d'hydrocarbures polyaromatiques dans le domaine 10-3--10 Torr,
Thermochimica Acta, 1989, 146, 53-61, https://doi.org/10.1016/0040-6031(89)87075-3
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Wieczorek and Kobayashi, 1981
Wieczorek, Stefan A.; Kobayashi, Riki,
Vapor-pressure measurements of 1-methylnaphthalene, 2-methylnaphthalene, and 9,10-dihydrophenanthrene at elevated temperatures,
J. Chem. Eng. Data, 1981, 26, 1, 8-11, https://doi.org/10.1021/je00023a005
. [all data]
Crafts, 1915
Crafts, J.M.,
J. Chim. Phys. Phys.-Chim. Biol., 1915, 13, 105. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
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]
Chickos, Annunziata, et al., 1986
Chickos, J.S.; Annunziata, R.; Ladon, L.H.; Hyman, A.S.; Liebman, J.F.,
Estimating heats of sublimation of hydrocarbons. A semiempirical approach,
J. Org. Chem., 1986, 51, 4311-4314. [all data]
Aihara, 1959
Aihara, A.,
Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy,
Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]
Bloink, Pausacker, et al., 1951
Bloink, G.J.; Pausacker, K.H.; Jones, A.S.; Lee, W.A.; Peacocke, A.R.; Bright, Norman F.H.; Moffatt, J.S.; Wilkinson, J.H.,
Notes,
J. Chem. Soc., 1951, 622, https://doi.org/10.1039/jr9510000622
. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.Z.,
Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]
Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Eykman, 1889
Eykman, J.F.,
Zur kryoskopischen Molekulargewichtsbestimmung,
Z. Physik. Chem., 1889, 4, 497-519. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [all data]
Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]
Terlouw, Heerma, et al., 1974
Terlouw, J.K.; Heerma, W.; Frintrop, P.C.M.; Dijkstra, G.; Meinema, H.A.,
Electron-impact induced fragmentation of some heterocyclic-tin compounds,
J. Organomet. Chem., 1974, 64, 205. [all data]
Bohlmann, Koppel, et al., 1974
Bohlmann, F.; Koppel, C.; Muller, B.; Schwarz, H.; Weyerstahl, P.,
Massenspektrometrische Untersuchung isomerer Kohlenwasserstoffe: Struktur und Bildungsenthalpie stabiler (C13H11+) Ionen,
Tetrahedron, 1974, 30, 1011. [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]
Pignataro, Mancini, et al., 1972
Pignataro, S.; Mancini, V.; Innorta, G.; Distefano, G.,
Ionization energies and ring orbital interaction in diarylmethanes and diaryleth,
Z. Naturforsch., 1972, 27, 534. [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]
Eaton and Traylor, 1974
Eaton, D.F.; Traylor, T.G.,
Distortional stabilization in phenyl participations,
J. Am. Chem. Soc., 1974, 96, 7109. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]
Pignataro, Mancini, et al., 1971
Pignataro, S.; Mancini, V.; Ridyard, J.N.A.; Lempka, H.J.,
Photoelectron energy spectra of molecules having classically non-conjugated π-systems,
Chem. Commun., 1971, 142. [all data]
Innorta, Torroni, et al., 1973
Innorta, G.; Torroni, S.; Pignataro, S.; Mancini, V.,
The activation energy as guiding factor in the fragmentation of substituted diphenylmethanes,
Org. Mass Spectrom., 1973, 7, 1399. [all data]
Rapp, Staab, et al., 1970
Rapp, U.; Staab, H.A.; Wunsche, C.,
Skelettumlagerungen unter Elektronenbeschuss-IV: zur Struktur der C13H9- und C12H9N-Ionen bei Benzylidenaminobenztriazolen,
Org. Mass Spectrom., 1970, 3, 45. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [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]
Giumanini, Verardo, et al., 2001
Giumanini, A.G.; Verardo, G.; Soják, L.; Kubinec, R.; Perjéssy, A.,
Identification of mononitro and dinitro isomers of diphenylmethane by GC-FT-IR and GC-MS techniques,
Ind. Eng. Chem. Res., 2001, 40, 6, 1449-1453, https://doi.org/10.1021/ie000667u
. [all data]
Tudor, 1997
Tudor, E.,
Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations,
J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6
. [all data]
van Haelst, van der Wielen, et al., 1996
van Haelst, Anniek G.; van der Wielen, Frans W.M.; Govers, Harrie A.J.,
Gas chromatographic determination of liquid vapour pressure and heat of vaporization of tetrachlorobenzyltoluenes,
Journal of Chromatography A, 1996, 727, 2, 265-273, https://doi.org/10.1016/0021-9673(95)01146-3
. [all data]
Gerasimenko, Kirilenko, et al., 1981
Gerasimenko, V.A.; Kirilenko, A.V.; Nabivach, V.M.,
Capillary gas chromatography of aromatic compounds found in coal tar fractions,
J. Chromatogr., 1981, 208, 1, 9-16, https://doi.org/10.1016/S0021-9673(00)87953-4
. [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]
Toda, Mihara, et al., 1983
Toda, H.; Mihara, S.; Umano, K.; Shibamoto, T.,
Photochemical studies on jasmin oil,
J. Agric. Food Chem., 1983, 31, 3, 554-558, https://doi.org/10.1021/jf00117a022
. [all data]
Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P.,
Use of incremental models to estimate the retention indexes of aromatic compounds,
Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946
. [all data]
Shapi and Hesso, 1990
Shapi, M.M.; Hesso, A.,
Thermal decomposition of polystyrene volatile compounds from large-scale pyrolysis,
J. Anal. Appl. Pyrolysis, 1990, 18, 2, 143-161, https://doi.org/10.1016/0165-2370(90)80004-8
. [all data]
Helmig, Bocquet, et al., 2004
Helmig, D.; Bocquet, F.; Pollmann, J.; Revermann, T.,
Analytical techniques for sesquiterpene emission rate studies in vegetation enclosure experiments,
Atmos. Environ., 2004, 38, 4, 557-572, https://doi.org/10.1016/j.atmosenv.2003.10.012
. [all data]
Nabivach and Gerasimenko, 1996
Nabivach, V.M.; Gerasimenko, V.A.,
Gas chromatographic retention characteristics of bicyclic aromatic hydrocarbons,
Coke and Chemistry (Rus), 1996, 6, 27-31. [all data]
Elizalde-González, Hutfliess, et al., 1996
Elizalde-González, M.P.; Hutfliess, M.; Hedden, K.,
Retention index system, adsorption characteristics, and sructure correlations of polycyclic aromatic hydrocarbons in fuels,
J. Hi. Res. Chromatogr., 1996, 19, 6, 345-352, https://doi.org/10.1002/jhrc.1240190608
. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Grigor'ev, Bozhko, et al., 2009
Grigor'ev, A.M.; Bozhko, E.S.; Rudakova, L.V.,
Use of correlation between retention indices on low-polarity phases for screening comp-lex mixtures by gas chromatography-mass spectrometry,
Rus. J. Anal. Chem., 2009, 64, 2, 140-143, https://doi.org/10.1134/S1061934809020087
. [all data]
Helmig, Revermann, et al., 2003
Helmig, D.; Revermann, T.; Pollmann, J.; Kaltschmidt, O.; Hernández, A.J.; Bocquet, F.; David, D.,
Calibration system and analytical considerations for quantitative sesquiterpene measurements in air,
J. Chromatogr. A, 2003, 1002, 1-2, 193-211, https://doi.org/10.1016/S0021-9673(03)00619-8
. [all data]
Peng, 1996
Peng, C.T.,
Gas chromatographic identification of aromatic hydrocarbons
in Liquid Scintillation Spectrometry, Cook, G.T.; Harkness, D.D.; MacKenzie, A.B.; Miller, B.F.; Scott, E.M., ed(s)., 1996, 221-232. [all data]
Zenkevich, 1994
Zenkevich, I.G.,
Contemporary State of Informational Maintenance for Gas Chromatographic Identification of Chlorinated Polycyclic Aromatic Compounds,
Zh. Ecol. Khim., 1994, 3, 2, 111-119. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S.,
Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods,
Chem. Anal., 2007, 52, 141-156. [all data]
Shao, Wang, et al., 2006
Shao, X.; Wang, G.; Sun, Y.; Zhang, R.; Xie, K.; Liu, H.,
Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MS,
J. Chromatogr. Sci., 2006, 44, 3, 141-147, https://doi.org/10.1093/chromsci/44.3.141
. [all data]
Marynowski, Pieta, et al., 2004
Marynowski, L.; Pieta, M.; Janeczek, J.,
Composition and source of polycyclic aromatic compounds in deposited dust from selected sites around the Upper Silesia, Poland,
Geol. Q., 2004, 48, 2, 169-180. [all data]
Piao, Chu, et al., 1999
Piao, M.; Chu, S.; Zheng, M.; Xu, X.,
Characterization of the combustion products of polyethylene,
Chemosphere, 1999, 39, 9, 1497-1512, https://doi.org/10.1016/S0045-6535(99)00054-5
. [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]
Bundt, Herbel, et al., 1991
Bundt, J.; Herbel, W.; Steinhart, H.; Franke, S.; Francke, W.,
Structure-type separation of diesel fuels by solid phase extraction and identification of the two- and three-ring aromatics by capillary GC-mass spectrometry,
J. Hi. Res. Chromatogr., 1991, 14, 2, 91-98, https://doi.org/10.1002/jhrc.1240140205
. [all data]
Guillén, Blanco, et al., 1989
Guillén, M.D.; Blanco, J.; Bermejo, J.; Blanco, C.G.,
Temperature programmed retention indices of some PAHs on Capillary columns coated with OV-1701 and SE-54,
J. Hi. Res. Chromatogr., 1989, 12, 8, 552-554, https://doi.org/10.1002/jhrc.1240120816
. [all data]
Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M.,
Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons,
Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity Pc Critical pressure S°gas Entropy of gas at standard conditions T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Vc Critical volume ΔfH°gas Enthalpy of formation of gas at standard conditions 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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