Diphenylmethane

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Condensed phase thermochemistry data

Go To: Top, Reaction thermochemistry 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid23.2 ± 0.53kcal/molReviewRoux, Temprado, et al., 2008There 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
Δfliquid23.2 ± 0.33kcal/molCcbSteele, Chirico, et al., 1995ALS
Δfliquid21.25kcal/molCcbParks and Mosley, 1950see Parks, West, et al., 1946; ALS
Quantity Value Units Method Reference Comment
Δcliquid-1655.6 ± 0.33kcal/molCcbSteele, Chirico, et al., 1995Corresponding Δfliquid = 23.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1653.83 ± 0.32kcal/molCcbParks and Mosley, 1950see Parks, West, et al., 1946; Corresponding Δfliquid = 21.28 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Δfsolid17.9 ± 0.53kcal/molReviewRoux, Temprado, et al., 2008There 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
Δfsolid27.3kcal/molCcbSchmidlin, 1906ALS
Quantity Value Units Method Reference Comment
Δcsolid-1595.kcal/molCcbSerijan and Wise, 1951Corresponding Δfsolid = -38. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1656.6kcal/molCcbWise, Serijan, et al., 1951Corresponding Δfsolid = 24.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1656.20 ± 0.20kcal/molCcbCoops, Mulder, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -1655.6 ± 0.2 kcal/mol; Corresponding Δfsolid = 23.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1659.9kcal/molCcbSchmidlin, 1906Corresponding Δfsolid = 27.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar57.19cal/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 77.86 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
63.60303.Duff and Everett, 1956T = 303 to 353 K.; DH
66.90300.Kurbatov, 1950T = 29 to 254°C.; DH
55.81298.5Smith and Andrews, 1931T = 102 to 322 K. Value is unsmoothed experimental datum.; DH
53.49282.5Huffman, Parks, et al., 1930T = 89 to 312 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry 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. 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

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

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

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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]

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]

Schmidlin, 1906
Schmidlin, M.J., Recherches chimiques et thermochimiques sur la constitution des rosanilines, Ann. Chim. Phys., 1906, 1, 195-256. [all data]

Serijan and Wise, 1951
Serijan, K.T.; Wise, P.H., Dicyclic hydrocarbons. III. Diphenyl- and dicyclohexylalkanes through C15, J. Am. Chem. Soc., 1951, 73, 4766-4769. [all data]

Wise, Serijan, et al., 1951
Wise, C.H.; Serijan, K.T.; Goodman, I.A., NACA Technical Report 1003, NACA Technical Report 1003, 1951, 1-10. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Duff and Everett, 1956
Duff, G.M.; Everett, D.H., The heat capacity of the system benzene + diphenylmethane, Trans. Faraday Soc., 1956, 52, 753-763. [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]

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]

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]

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]


Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References