Diphenylmethane

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Phase change data

Go To: Top, Gas phase ion energetics data, Ion clustering 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 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
Tboil535. ± 4.KAVGN/AAverage of 51 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus299. ± 2.KAVGN/AAverage of 83 out of 85 values; Individual data points
Quantity Value Units Method Reference Comment
Tc780. ± 60.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Pc27. ± 3.atmN/ATsonopoulos and Ambrose, 1995 
Pc26.75atmN/AWieczorek and Kobayashi, 1980Uncertainty assigned by TRC = 2.96 atm; TRC
Pc59.0000atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3.0000 atm; TRC
Pc28.2000atmN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 0.99995 atm; TRC
Pc28.2000atmN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 0.99995 atm; TRC
Quantity Value Units Method Reference Comment
Vc0.563l/molN/ATsonopoulos and Ambrose, 1995 
Quantity Value Units Method Reference Comment
ρc1.8 ± 0.3mol/lN/ATsonopoulos and Ambrose, 1995 
ρc1.780mol/lN/AStephenson, 1992Uncertainty assigned by TRC = 0.12 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap16. ± 2.kcal/molAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Δsub20.8 ± 0.2kcal/molReviewRoux, Temprado, et al., 2008There 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
Δsub20.9 ± 0.2kcal/molN/AVerevkin, 1999AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
15.3 ± 0.02340.IP,EBChirico and Steele, 2005Based on data from 330. to 588. K.; AC
14.6 ± 0.02380.IP,EBChirico and Steele, 2005Based on data from 330. to 588. K.; AC
13.8 ± 0.02420.IP,EBChirico and Steele, 2005Based on data from 330. to 588. K.; AC
13.1 ± 0.02460.IP,EBChirico and Steele, 2005Based on data from 330. to 588. K.; AC
12.4 ± 0.05500.IP,EBChirico and Steele, 2005Based on data from 330. to 588. K.; AC
11.7 ± 0.07540.IP,EBChirico and Steele, 2005Based on data from 330. to 588. K.; AC
15.9 ± 0.1323.GSVerevkin, 1999Based on data from 303. to 343. K.; AC
14.8368.N/ASohda, Okazaki, et al., 1990Based on data from 353. to 433. K.; AC
15.2363.N/ASasse, N'guimbi, et al., 1989Based on data from 303. to 402. K.; AC
17.3310.AStephenson and Malanowski, 1987Based on data from 295. to 383. K.; AC
13.6438.AStephenson and Malanowski, 1987Based on data from 423. to 583. K.; AC
13.3445.N/AWieczorek and Kobayashi, 1981AC
11.7535.N/AWieczorek and Kobayashi, 1981AC
13.0505.N/ACrafts, 1915Based 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 ± 0.2284.GSVerevkin, 1999Based on data from 273. to 295. K.; AC
17.1286.EMSasse, N'guimbi, et al., 1989Based on data from 273. to 298. K.; AC
19.9 ± 0.79286.HSAChickos, Annunziata, et al., 1986Based on data from 276. to 295. K.; AC
19.71 ± 0.15299.8VAihara, 1959crystal phase; ALS
15.3278. to 299.N/ABloink, Pausacker, et al., 1951See also Jones, 1960.; AC
17.2 ± 0.2297.N/AWolf and Weghofer, 1938AC
17.2 ± 0.2297.VWolf and Weghofer, 1938, 2ALS

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
4.543298.4N/AChirico and Steele, 2005AC
4.441298.3ACDomalski and Hearing, 1996AC
4.4381298.3N/AHuffman, Parks, et al., 1930DH
4.5531299.4N/AEykman, 1889DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
14.90298.3Domalski and Hearing, 1996CAL
14.88298.3Huffman, Parks, et al., 1930DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics data

Go To: Top, Phase change data, Ion clustering data, 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)191.7kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity183.9kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
<0.156 ± 0.043ECDWojnarovits and Foldiak, 1981EA 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
9.4EITerlouw, Heerma, et al., 1974LLK
8.7 ± 0.1EIBohlmann, Koppel, et al., 1974LLK
8.55 ± 0.03PIPotapov, Kardash, et al., 1972LLK
9.00 ± 0.05EIPignataro, Mancini, et al., 1972LLK
8.67 ± 0.05PEDistefano, Pignataro, et al., 1976Vertical value; LLK
8.8PEEaton and Traylor, 1974Vertical value; LLK
8.80 ± 0.02PEMaier and Turner, 1973Vertical value; LLK
9.1PEPignataro, Mancini, et al., 1971Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+11.5 ± 0.1C6H5EIInnorta, Torroni, et al., 1973LLK
C13H9+14.9 ± 0.1H2+HEIRapp, Staab, et al., 1970RDSH
C13H11+11.2 ± 0.1HEIBohlmann, Koppel, et al., 1974LLK

De-protonation reactions

C13H11- + Hydrogen cation = Diphenylmethane

By formula: C13H11- + H+ = C13H12

Quantity Value Units Method Reference Comment
Δr363.6 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr361.3 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr358.2 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr355.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

Ion clustering data

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 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

Chlorine anion + Diphenylmethane = (Chlorine anion • Diphenylmethane)

By formula: Cl- + C13H12 = (Cl- • C13H12)

Quantity Value Units Method Reference Comment
Δr7.40kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
7.4300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

References

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, 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, 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]

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]

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]


Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References