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Azuliporphyrin: A Case of Borderline Porphyrinoid Aromaticity
Author(s) -
Lash Timothy D.,
Chaney Sun T.
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199708391
Subject(s) - azulene , aromaticity , limiting , ring (chemistry) , protonation , conjugated system , character (mathematics) , diamagnetism , chemistry , ring current , crystallography , computational chemistry , stereochemistry , chemical physics , molecule , photochemistry , organic chemistry , physics , mathematics , quantum mechanics , geometry , mechanical engineering , ion , earth's magnetic field , magnetic field , engineering , polymer
Through “electronic separation” of the seven‐membered ring the formally cross‐conjugated, azulene‐containing macrocycle (limiting structure A ) becomes a porphyrinlike species with a weak, diamagnetic ring current (limiting structure B ). This aromatic character is further accentuated upon twofold protonation.