The synthesis of a new chiral porphyrin, meso-tetra(α, β, α, β-o-camphanylamidophenyl)porphyrin, and its Mn(III) and Rh(III) derivatives is reported. Complete resonance assignments of both the 1H and 13C spectra of the ligand has been achieved via homo- and hetero-nuclear 2D NMR. Insertion of metal ions into the porphyrin ring was performed both in order to test the catalytic properties of the resulting complexes and to characterize the effect of of metal coordination on the spatial distribution of the bulky substituents. The Mn complex was then tested in catalytic chiral epoxidation reactions, giving low enantiomeric excesses (20%). The 2D NMR spectra of the Rh derivative indicate the existence of four molecular species generated by the interaction of the metal atom with the peripheral substituents of the porhyrin ring. In fact, a complex combination of axial coordination, together with the chirality of the camphanyl substituents, removed the symmetry of the porphyrin plane.

Licoccia, S., Paci, M., Tagliatesta, P., Paolesse, R., Antonaroli, S., Boschi, T. (1991). 1H and13C NMR characterization of a new chiral porphyrin,meso-Tetra(α, β, α, β-o-camphanylamidophenyl)porphyrin, and its rhodium(III) complex. MAGNETIC RESONANCE IN CHEMISTRY, 29(11), 1084-1091 [10.1002/mrc.1260291103].

1H and13C NMR characterization of a new chiral porphyrin,meso-Tetra(α, β, α, β-o-camphanylamidophenyl)porphyrin, and its rhodium(III) complex

LICOCCIA, SILVIA;PACI, MAURIZIO;TAGLIATESTA, PIETRO;PAOLESSE, ROBERTO;ANTONAROLI, SIMONETTA;BOSCHI, TRISTANO
1991-01-01

Abstract

The synthesis of a new chiral porphyrin, meso-tetra(α, β, α, β-o-camphanylamidophenyl)porphyrin, and its Mn(III) and Rh(III) derivatives is reported. Complete resonance assignments of both the 1H and 13C spectra of the ligand has been achieved via homo- and hetero-nuclear 2D NMR. Insertion of metal ions into the porphyrin ring was performed both in order to test the catalytic properties of the resulting complexes and to characterize the effect of of metal coordination on the spatial distribution of the bulky substituents. The Mn complex was then tested in catalytic chiral epoxidation reactions, giving low enantiomeric excesses (20%). The 2D NMR spectra of the Rh derivative indicate the existence of four molecular species generated by the interaction of the metal atom with the peripheral substituents of the porhyrin ring. In fact, a complex combination of axial coordination, together with the chirality of the camphanyl substituents, removed the symmetry of the porphyrin plane.
1991
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/03 - CHIMICA GENERALE E INORGANICA
English
Con Impact Factor ISI
meso-Tetra(α, β, α, β-o-camphanylamidophenyl)porphyrin; Rhodium complex; Catalysis; 1H and 13C NMR
Licoccia, S., Paci, M., Tagliatesta, P., Paolesse, R., Antonaroli, S., Boschi, T. (1991). 1H and13C NMR characterization of a new chiral porphyrin,meso-Tetra(α, β, α, β-o-camphanylamidophenyl)porphyrin, and its rhodium(III) complex. MAGNETIC RESONANCE IN CHEMISTRY, 29(11), 1084-1091 [10.1002/mrc.1260291103].
Licoccia, S; Paci, M; Tagliatesta, P; Paolesse, R; Antonaroli, S; Boschi, T
Articolo su rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/104628
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