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• W2001520888 abstract "This study advances strategy and design in catalysts and reagents for fluorous and supercritical CO(2) chemistry by defining the structural requirements for insulating a typical active site from a perfluoroalkyl segment. The vertical ionization potentials of the phosphines P((CH(2))(m)R(f8))(3) (m = 2 (2) to 5 (5)) are measured by photoelectron spectroscopy, and the enthalpies of protonation by calorimetry (CF(3)SO(3)H, CF(3)C(6)H(5)). They undergo progressively more facile (energetically) ionization and protonation (P(CH(2)CH(3))(3) > 5 > 4 approximately equal to P(CH(3))(3) > 3 > 2), as expected from inductive effects. Equilibrations of trans-Rh(CO)(Cl)(L)(2) complexes (L = 2, 3) establish analogous Lewis basicities. Density functional theory is used to calculate the structures, energies, ionization potentials, and gas-phase proton affinities (PA) of the model phosphines P((CH(2))(m)()CF(3))(3) (2'-9'). The ionization potentials of 2'-5' are in good agreement with those of 2-5, and together with PA values and analyses of homodesmotic relationships are used to address the title question. Between 8 and 10 methylene groups are needed to effectively insulate a perfluoroalkyl segment from a phosphorus lone pair, depending upon the criterion employed. Computations also show that the first carbon of a perfluoroalkyl segment exhibits a much greater inductive effect than the second, and that ionization potentials of nonfluorinated phosphines P((CH(2))(m)CH(3))(3) reach a limit at approximately nine carbons (m = 8)." @default.
• W2001520888 created "2016-06-24" @default.
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• W2001520888 date "2002-01-19" @default.
• W2001520888 modified "2023-10-18" @default.
• W2001520888 title "How To Insulate a Reactive Site from a Perfluoroalkyl Group: Photoelectron Spectroscopy, Calorimetric, and Computational Studies of Long-Range Electronic Effects in Fluorous Phosphines P((CH₂)<i>_m</i>(CF₂)₇CF₃)₃" @default.
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• W2001520888 doi "https://doi.org/10.1021/ja011877g" @default.
• W2001520888 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11841323" @default.
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