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An Overall Comprehension of Anti‐Aromatic Porphyrinoids Using 3D‐Graphical Chemical Shielding Description
Author(s) -
Qi Dongdong,
Jiang Jianzhuang
Publication year - 2020
Publication title -
advanced theory and simulations
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.068
H-Index - 17
ISSN - 2513-0390
DOI - 10.1002/adts.202000007
Subject(s) - pyrrole , aromaticity , ring (chemistry) , benzene , chemistry , computational chemistry , organic chemistry , molecule
A systematic investigation to rank the anti‐aromatic porphyrinoids is performed. Based on density functional theory calculations, four rules are summarized to obtain the highest anti‐aromatic porphyrinoids: 1) the replacement from meso‐C to meso‐(─C≡C─), 2) the replacement from pyrrole unit to inner‐N to inner‐O, 3) the replacement from two opposite meso‐C/N atoms to two pyrrole units, and 4) the replacement from one pyrrole ring to a carbonyl benzene ring. It is worth noting that the long chain with alternating single/double bonds is not beneficial or harmful to the anti‐aromaticity.