Bibenzyl

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Gas phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas32.41 ± 0.31kcal/molCcbColeman and Pilcher, 1966ALS
Δfgas30.83kcal/molN/AParks, West, et al., 1946Value computed using ΔfHsolid° value of 44.9±3.1 kj/mol from Parks, West, et al., 1946 and ΔsubH° value of 84.1 kj/mol from Coleman and Pilcher, 1966.; DRB

Condensed phase thermochemistry data

Go To: Top, Gas 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:
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
Δcliquid-1807.5 ± 1.8kcal/molCcbBanse and Parks, 1933Reanalyzed by Cox and Pilcher, 1970, Original value = -1806.97 kcal/mol; Corresponding Δfliquid = 12.58 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Δfsolid12.31 ± 0.31kcal/molCcbColeman and Pilcher, 1966ALS
Δfsolid10.72 ± 0.73kcal/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = 10.53 ± 0.004 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcsolid-1807.24 ± 0.26kcal/molCcbColeman and Pilcher, 1966Corresponding Δfsolid = 12.32 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1806.8 ± 0.24kcal/molCcbCoops, Mulder, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -1807. ± 0.2 kcal/mol; See Coops, Mulder, et al., 1946; Corresponding Δfsolid = 11.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1740.kcal/molCcbSerijan and Wise, 1951Corresponding Δfsolid = -55. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1815.1kcal/molCcbWise, Serijan, et al., 1951Corresponding Δfsolid = 20.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1805.64 ± 0.72kcal/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -1805.48 ± 0.72 kcal/mol; Corresponding Δfsolid = 10.72 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar63.9080cal/mol*KN/AMesserly, Finke, et al., 1988crystaline, I phase; DH
solid,1 bar64.60cal/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 90.37 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
60.6511298.15Messerly, Finke, et al., 1988crystaline, I phase; T = 10 to 400 K.; DH
76.51330.Kurbatov, 1950Temperature 54 to 254°C. Mp = 52.8°C.; DH
60.21298.1Schmidt, 1941T = 20 to 200°C, equations only in t°C. Cp(c) = 0.2867 + 0.001743t cal/g*K (20 to 51°C); Cp(liq) = 0.3865 + 0.0005986t cal/g*K (51 to -200°C).; DH
61.42303.Ferry and Thomas, 1933T = 303 to 343 K.; DH
60.61298.5Smith and Andrews, 1931T = 102 to 299 K. Value is unsmoothed experimental datum.; DH
59.99293.6Huffman, Parks, et al., 1930T = 93 to 294 K. Value is unsmoothed experimental datum.; DH

Gas phase ion energetics data

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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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
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)191.6kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity185.0kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.00 ± 0.05EIPignataro, Mancini, et al., 1972LLK
8.7 ± 0.1EIMcLafferty, Wachs, et al., 1970RDSH
9.1PEPignataro, Mancini, et al., 1971Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+10.6C7H7EIMcLafferty, Wachs, et al., 1970RDSH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase 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.

Coleman and Pilcher, 1966
Coleman, D.J.; Pilcher, G., Heats of combustion of biphenyl, bibenzyl, naphthalene, anthracene, and phenanthrene, Trans. Faraday Soc., 1966, 62, 821-827. [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]

Banse and Parks, 1933
Banse, H.; Parks, G.S., Thermal data on organic compounds. XII. The heats of combustion of nine hydrocarbons, J. Am. Chem. Soc., 1933, 55, 3223-3227. [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]

Coops, Mulder, et al., 1953
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J., Thermochemical investigations on arylethanes I. Heats of combustion of phenylethanes., Rec. Trav. Chim. Pays/Bas, 1953, 72, 785. [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]

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]

Messerly, Finke, et al., 1988
Messerly, J.F.; Finke, H.L.; Good, W.D.; Gammon, B.E., Condensed-phase heat capacities and derived thermodynamic properties for 1,4-dimethylbenzene, 1,2-diphenylethane, and 2,3-dimethylnaphthalene, J. Chem. Thermodynam., 1988, 20, 485-501. [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]

Schmidt, 1941
Schmidt, W.R., Thesis Washington University (St. Louis), 1941. [all data]

Ferry and Thomas, 1933
Ferry, J.D.; Thomas, S.B., Some heat capacity data for durene, pentamethylbenzene, stilbene, and dibenzyl, J. Phys. Chem., 1933, 37, 253-255. [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]

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]

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]

McLafferty, Wachs, et al., 1970
McLafferty, F.W.; Wachs, T.; Lifshitz, C.; Innorta, G.; Irving, P., Substituent effects in unimolecular ion decompositions. XV. Mechanistic interpretations and the quasi-equilibrium theory, J. Am. Chem. Soc., 1970, 92, 6867. [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]


Notes

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