Theoretical Investigation of Aromaticity in Porphyrin Compounds
In this article,the aromaticity of porphin,dideazaporphyrin and pyrrole compounds was studied by theoretical methods.Anisotropy of Induced Current Density showed that the induced ring currents of Porphin and dideazaporphyrin were very similar,so their 1H NMR spectra were also very similar.The aromatic stabilization energy of pyrrole monomer is higher than that of dideazaporphyrin,and the aromatic stabilization energy of porphin is almost equal to the sum of the aromatic stabilization energy of the two pyrrole and dideazaporphyrin.AdNDP analysis showed that porphin has two 5-center-2 electron π bonds in each pyrrole ring of porphin and five 18-center-2 electron π bonds on the macrocycle ring.This indicated that in addition to the aromaticity of pyrrole ring,macrocycle also had aromaticity.Therefore,it can be inferred that the aromaticity of porphin is more complex than that of dideazaporphyrin.It cannot be considered that the aromaticity of porphyrin is similar to that of dideadaporphyrin.
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