49757-42-8Relevant articles and documents
Halogen Transfer to Carbon Radicals by High-Valent Iron Chloride and Iron Fluoride Corroles
Farley, Geoffrey W.,Siegler, Maxime A.,Goldberg, David P.
, p. 17288 - 17302 (2021/11/17)
High-valent iron halide corroles were examined to determine their reactivity with carbon radicals and their ability to undergo radical rebound-like processes. Beginning with Fe(Cl)(ttppc) (1) (ttppc = 5,10,15-tris(2,4,6-triphenylphenyl)corrolato3-), the new iron corroles Fe(OTf)(ttppc) (2), Fe(OTf)(ttppc)(AgOTf) (3), and Fe(F)(ttppc) (4) were synthesized. Complexes 3 and 4 are the first iron triflate and iron fluoride corroles to be structurally characterized by single crystal X-ray diffraction. The structure of 3 reveals an AgI-pyrrole (η2-π) interaction. The Fe(Cl)(ttppc) and Fe(F)(ttppc) complexes undergo halogen transfer to triarylmethyl radicals, and kinetic analysis of the reaction between (p-OMe-C6H4)3C?and 1 gave k = 1.34(3) × 103 M-1 s-1 at 23 °C and 2.2(2) M-1 s-1 at -60 °C, ΔHL = +9.8(3) kcal mol-1, and ΔSL = -14(1) cal mol-1 K-1 through an Eyring analysis. Complex 4 is significantly more reactive, giving k = 1.16(6) × 105 M-1 s-1 at 23 °C. The data point to a concerted mechanism and show the trend X = F- > Cl- > OH- for Fe(X)(ttppc). This study provides mechanistic insights into halogen rebound for an iron porphyrinoid complex.
Synthesis and biological evaluation of novel N-substituted nipecotic acid derivatives with an alkyne spacer as GABA uptake inhibitors
Tóth, Krisztián,H?fner, Georg,Wanner, Klaus T.
, p. 3668 - 3687 (2018/06/19)
In this study, we present the synthesis and structure–activity relationships (SAR) of novel N-substituted nipecotic acid derivatives closely related to (S)-SNAP-5114 (2) in the pursuit of finding new and potent mGAT4 selective inhibitors. By the use of iminium ion chemistry, a series of new N-substituted nipecotic acid derivatives containing a variety of heterocycles, and an alkyne spacer were synthesized. Biological evaluation of the prepared compounds showed, how the inhibitory potency and subtype selectivity for the murine GABA transporters (mGATs) were influenced by the performed modifications.
Synthesis, crystal structure, and luminescence of tetrakis(4-methoxyphenyl) methane
Guieu, Samuel,Rocha, Jo?o,Silva, Artur M.S.
, p. 2870 - 2873 (2013/06/26)
A new synthesis of a tetrahedral tecton, tetrakis(4-methoxyphenyl)methane, is reported. This compound exhibits a strong fluorescence around 340 nm at room temperature, both in solution and in the solid state. Upon crystallization, another luminescence band can be observed around 500 nm, attributed to phosphorescence. A study of the single-crystal structure of the compound provided a rationalization of this crystallization induced phosphorescence. The crystal of tetrakis(4-methoxyphenyl)methane belongs to the tetragonal space group P4?21c, and the structural analysis revealed a close packing of the molecules, with no void space and no solvent molecules in the crystal. The molecules are held together in a columnar array via multiple C-Ha?π hydrogen bonds. The hydrogen bonds between the molecules impede the torsional vibrations of the aromatic rings, preventing thermal relaxation from the triplet state, and hence promoting phosphorescence at room temperature.
