Regiospecific naphthyl nitration of 5,10,15,20‐tetranaphthylporphyrin |
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| Authors: | Jun Li Gerhard Raabe Gao‐mai Yang Ming‐yue Duan Giuseppe Mele Feng‐xing Zhang |
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| Institution: | 1. Key Laboratory of Synthetic and Natural Functional Molecular Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, P. R. China;2. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D‐52074 Aachen, Germany;3. Dipartimento di Ingegneria dell'Innovazione, Università del Salento, Via Arnesano, 73100 Lecce, Italy |
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| 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% HNO3. The 1H‐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. Copyright © 2010 John Wiley & Sons, Ltd. |
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| Keywords: | ab initio asymmetry nitration nitronaphthylporphyrin quantum‐chemical calculations synthesis tetranaphthylporphyrin (TNP) |
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