The nitration reaction of 5,10,15,20-tetranaphthylporphyrin (TNP) was investigated in detail and the mono-, di-, and tri-nitro-TNPs were synthesized in high yield using 65% HNO(3). The (1)H-NMR study shows that the preferred site of nitration of the naphthyl substituted porphyrin is the carbon atom of the meso-substituents para to its bond to the porphyrin ring. The reaction leads to exquisite regioselectivity in favor of the mono, di, and tri-nitro-TNP. Quantum-chemical ab initio calculations at different levels of theory were performed in order to explain the experimentally observed reactivity.
REGIOSPECIFIC NAPHTHYL NITRATION OF 5,10,15,20- TETRANAPHTHYLPORPHYRIN
MELE, Giuseppe Agostino;
2011-01-01
Abstract
The nitration reaction of 5,10,15,20-tetranaphthylporphyrin (TNP) was investigated in detail and the mono-, di-, and tri-nitro-TNPs were synthesized in high yield using 65% HNO(3). The (1)H-NMR study shows that the preferred site of nitration of the naphthyl substituted porphyrin is the carbon atom of the meso-substituents para to its bond to the porphyrin ring. The reaction leads to exquisite regioselectivity in favor of the mono, di, and tri-nitro-TNP. Quantum-chemical ab initio calculations at different levels of theory were performed in order to explain the experimentally observed reactivity.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
