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
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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

References

Go To: Top, Phase change 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.

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]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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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