Phosphine, triphenyl-

• Formula: C₁₈H₁₅P
• Molecular weight: 262.2855
• IUPAC Standard InChI: InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Copy

  
• IUPAC Standard InChIKey: RIOQSEWOXXDEQQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 603-35-0
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Triphenylphosphine; Triphenylphosphorus; Trifenylfosfin; Triphenylphosphide; Triphenylphosphane; Phosphorus triphenyl; NSC 10; NSC 215203; PP 360
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry 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 compiled by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Phase change 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 compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (MINERAL OIL MULL) $$ SPECTRAL FEATURE AROUND 3000 CM^-1 IS SKETCHED FROM PELLET DATA, THE OIL MULL SPECTRUM DOES NOT SHOW THE SPLIT FEATURE; PERKIN-ELMER; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLUTION (11% CCl4 FOR 3800-1300, 11% CS2 FOR 1300-650, AND 11% CCl4 FOR 650-250); PERKIN-ELMER 521 (GRATING); 2 cm^-1 resolution

Mass spectrum (electron ionization)

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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 compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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 compiled by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H., Thermal energy studies. II. Phenyl derivatives of metals, J. Am. Chem. Soc., 1931, 53, 3661-3667. [all data]

Kirklin and Domalski, 1988
Kirklin, D.R.; Domalski, E.S., Enthalpies of combustion of triphenylphosphine and triphenylphosphine oxide, J. Chem. Thermodyn., 1988, 20, 743. [all data]

Forward, Bowden, et al., 1949
Forward, M.V.; Bowden, S.T.; Jones, W.J., Physical Properties of Triphenyl Compounds of Group VB Elements, J. Chem. Soc., 1949, 1949, 121-6. [all data]

Smith and Andrews, 1931, 2
Smith, R.H.; Andrews, D.H., Thermal Energy Studies II. Phenyl Derivatives of Metals, J. Am. Chem. Soc., 1931, 53, 3661-7. [all data]

Kirklin and Domalski, 1988, 2
Kirklin, D.R.; Domalski, E.S., Enthalpies of combustion of triphenylphosphine and triphenylphosphine oxide, J. Chem. Thermodynam., 1988, 20, 743-754. [all data]

Pilcher and Skinner, 1983
Pilcher, G.; Skinner, H.A., Thermochemistry of organometallic compounds, 1983, 43-90, https://doi.org/10.1002/9780470771686.ch2 . [all data]

Bedford and Mortimer, 1960
Bedford, A.F.; Mortimer, C.T., 327. Heats of formation and bond energies. Part II. Triethyl phosphate, triphenylphosphine, and triphenylphosphine oxide, J. Chem. Soc., 1960, 1622, https://doi.org/10.1039/jr9600001622 . [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]

Forward, Bowden, et al., 1949, 2
Forward, M.V.; Bowden, S.T.; Jones, W.J., S 26. Physical properties of triphenyl compounds of group V B elements, J. Chem. Soc., 1949, S121, https://doi.org/10.1039/jr949000s121 . [all data]

De Kruif, Herman, et al., 1981
De Kruif, Kees G.; Herman, Johan M.; Van den Berg, Pieter J., Enthalpies of vaporization and vapor pressures of triphenyl-, tri(p-tolyl)- and tris(2-cyanoethyl)phosphines, J. Chem. Eng. Data, 1981, 26, 4, 359-361, https://doi.org/10.1021/je00026a002 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [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]

Potapov, Rodionov, et al., 1974
Potapov, V.K.; Rodionov, A.N.; Evlasheva, T.I.; Rogozhin, K.L., Photoionization of triphenyl derivatives of elements in group VB of the periodic table, High Energy Chem., 1974, 8, 486, In original 559. [all data]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. III. Bonding with Group V substituents, Inorg. Chem., 1974, 13, 308. [all data]

Muller and Fenderl, 1969
Muller, J.; Fenderl, K., Massenspektren und Ionisierungspotentiale von C₅H₅Mn(CO)₂PX₃-Komplexen, J. Organometal. Chem., 1969, 19, 123. [all data]

Distefano, Innorta, et al., 1968
Distefano, G.; Innorta, G.; Pignataro, S.; Foffani, A., Correlation between the ionization potentials of transition metal complexes and of the corresponding ligands, J. Organometal. Chem., 1968, 14, 165. [all data]

Vilesov and Zaitsev, 1964
Vilesov, F.I.; Zaitsev, V.M., Photoionization of phenyl derivatives of group 5 elements, Dokl. Akad. Nauk SSSR, 1964, 154, 886, In original 117. [all data]

Ikuta, Kebarle, et al., 1982
Ikuta, S.; Kebarle, P.; Bancroft, G.M.; Chan, T.; Puddephatt, R.J., Basicities of methyl-, methylphenyl-, and phenylphosphines in the gas phase, J. Am. Chem. Soc., 1982, 104, 5899. [all data]

Daamen, Oskam, et al., 1980
Daamen, H.; Oskam, A.; Stufkens, D.J., U.V. photoelectron (He I and He II) studies of M(CO)₅PR₃ (M = Cr, W and R = C₆H₁₁, C₆H₅, O-i-C₃H₇, OC₆H₅) and W(CO)₅As(C₆H₅)₃, Inorg. Chim. Acta, 1980, 38, 71. [all data]

Starzewski and Bock, 1976
Starzewski, K.A.O.; Bock, H., Photoelectron spectra and molecular properties. 58.^1,2 Phosphorus ylides: Gas phase ionization potentials and charge distribution, J. Am. Chem. Soc., 1976, 98, 8486. [all data]

Weiner, Lattman, et al., 1975
Weiner, M.A.; Lattman, M.; Grim, S.O., Ultraviolet photoelectron spectra of some substituted triarylphosphines, J. Org. Chem., 1975, 40, 1292. [all data]

Distefano, Pignataro, et al., 1975
Distefano, G.; Pignataro, S.; Szepes, L.; Borossay, J., Photoelectron spectroscopy study of the triphenyl derivatives of the group V elements, J. Organomet. Chem., 1975, 102, 313. [all data]

Jaffe and Freedman, 1952
Jaffe, H.H.; Freedman, L.D., J. Am. Chem. Soc., 1952, 74, 1069. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

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