Trimethylphosphine

• Formula: C₃H₉P
• Molecular weight: 76.0773
• IUPAC Standard InChI: InChI=1S/C3H9P/c1-4(2)3/h1-3H3 Copy

  
• IUPAC Standard InChIKey: YWWDBCBWQNCYNR-UHFFFAOYSA-N Copy
• CAS Registry Number: 594-09-2
• 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: Phosphine, trimethyl-; Trimethylphosphorus; (CH3)3P
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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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 by: William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Reaction 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: John E. Bartmess

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

C₃H₈P^- +  =

By formula: C₃H₈P^- + H⁺ = C₃H₉P

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:
B - John E. Bartmess
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

Appearance energy determinations

De-protonation reactions

C₃H₈P^- +  =

By formula: C₃H₈P^- + H⁺ = C₃H₉P

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

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, UV/Visible spectrum, Notes

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

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]

Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M., Gas-phase acidity of CH₃X [X = P(CH₃)₂, SCH₃, F, Cl, Br, I] compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 837. [all data]

Romer, Gatev, et al., 1998
Romer, B.; Gatev, G.G.; Zhong, M.; Brauman, J.I., Alpha-Stabilization by Silyl and Phosphino Substitution, J. Am. Chem. Soc., 1998, 120, 12, 2919, https://doi.org/10.1021/ja970279s . [all data]

Ingemann and Nibbering, 1985, 2
Ingemann, S.; Nibbering, N.M.M., Gas phase chemistry of alpha-thio carbanions, Can. J. Chem., 1985, 62, 2273. [all data]

Grabowski, Roy, et al., 1988
Grabowski, J.J.; Roy, P.D.; Leone, R., Trimethylphosphine: Anion-Molecule Reactions and Acidity in the Gas Phase, J. Chem. Soc. Perkin Trans., 1988, 2, 8, 1627, https://doi.org/10.1039/p29880001627 . [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]

Bancroft, Chan, et al., 1982
Bancroft, G.M.; Chan, T.; Puddephatt, R.J.; Tse, J.S., Role of the Au 5d orbitals in bonding: Photoelectron spectra of [AuMe(PMe₃)], Inorg. Chem., 1982, 21, 2946. [all data]

Hodges, McDonnell, et al., 1980
Hodges, R.V.; McDonnell, T.J.; Beauchamp, J.L., Properties reactions of trimethyl phosphite, trimethyl phosphate, triethyl phosphate, and trimethyl phosphorothionate by ion cyclotron resonance spectroscopy, J. Am. Chem. Soc., 1980, 102, 1327. [all data]

Hodges, Houle, et al., 1980
Hodges, R.V.; Houle, F.A.; Beauchamp, J.L.; Montag, R.A.; Verkade, J.G., Effects of molecular structure on basicity. Gas phase proton affinities of cyclic phosphites, J. Am. Chem. Soc., 1980, 102, 932. [all data]

Yarbrough and Hall, 1978
Yarbrough, L.W., II; Hall, M.B., Photoelectron spectra of substituted chromium, molybdenum, and tungsten pentacarbonyls. Relative π-acceptor and σ-donor properties of various phosphorus ligands, Inorg. Chem., 1978, 17, 2269. [all data]

Staley and Beauchamp, 1974
Staley, R.H.; Beauchamp, J.L., Basicities ion-molecule reactions of the methylphosphines in the gas phase by ion cyclotron resonance spectroscopy, J. Am. Chem. Soc., 1974, 96, 6252. [all data]

Wada and Kiser, 1964
Wada, Y.; Kiser, R.W., A mass spectrometric study of some alkyl-substituted phosphines, J. Phys. Chem., 1964, 68, 2290. [all data]

Fischler and Halmann, 1964
Fischler, J.; Halmann, M., Electron-impact studies of phosphorus compounds, J. Chem. Soc., 1964, 31. [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]

Elbel, Dieck, et al., 1982
Elbel, S.; Dieck, H.T.; Demuth, R., Photoelectron sSpectra of group V compounds. IX. The relative perfluoroalkyl substituent effect, J. Fluorine Chem., 1982, 19, 349. [all data]

Cowley, Kemp, et al., 1982
Cowley, A.H.; Kemp, R.A.; Lattman, M.; McKee, M.L., Lewis base behavior of methylated and fluorinated phosphines. A photoelectron spectroscopic investigation, Inorg. Chem., 1982, 21, 85. [all data]

Starzewski, Richter, et al., 1976
Starzewski, K.-H.A.O.; Richter, W.; Schmidbaur, H., Photoelektronenspektren und Struktur von Arsenyliden. P versus As: Ein Beitrag zur Problematik der ylidischen Bindung, Chem. Ber., 1976, 109, 473. [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]

Lappert, Pedley, et al., 1975
Lappert, M.F.; Pedley, J.B.; Wilkins, B.T.; Stelzer, O.; Unger, E., Bonding studies of compounds of boron and the group 3-5 elements. Part XIII. He(I) photoelectron spectra of phosphines R_nPX_3-n (R=Me or Bu'; X=H, Cl, or F; n=1-3), (Me₂N)_nPCl_3-n(n=1-3), and (R₂N)PF₂(R=Me or Et), J. Chem. Soc. Dalton Trans., 1975, 1207. [all data]

Elbel, Bergmann, et al., 1974
Elbel, S.; Bergmann, H.; EnBlin, W., Photoelectron spectra of the trimethyl compounds of the Group V elements, J. Chem. Soc. Faraday Trans. 2., 1974, 70, 555. [all data]

Schafer and Schweig, 1972
Schafer, W.; Schweig, A., Zur Konjugation in aromatischen Aminen und Phosphanen, Angew. Chem., 1972, 84, 898. [all data]

Cradock, Ebsworth, et al., 1972
Cradock, S.; Ebsworth, E.A.V.; Savage, W.J.; Whiteford, R.A., Photoelectron spectra of some methyl, silyl and germyl amines, phosphines and arsines, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 934. [all data]

Taft, Martin, et al., 1965
Taft, R.W.; Martin, R.H.; Lampe, F.W., Stabilization energies of substituted methyl cations. The effect of strong demand on the resonance order, J. Am. Chem. Soc., 1965, 87, 2490. [all data]

Halmann, 1963
Halmann, M., J. Chem. Soc., 1963, 2853. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, UV/Visible spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

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