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Molecular interaction between free base meso ‐tetraarylporphyrins and o ‐chloranil
Author(s) -
Dehghani Hossein,
Farshchian Mahmood
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.91
Subject(s) - chemistry , chloranil , porphyrin , lone pair , crystallography , yield (engineering) , molecule , chloroform , proton nmr , electron acceptor , acceptor , free base , photochemistry , stereochemistry , organic chemistry , salt (chemistry) , materials science , physics , metallurgy , condensed matter physics
Interaction of meso ‐tetraarylporphyrins (H 2 T(4‐X)PP, X=H, CH 3 , OCH 3 , Br) and o ‐chloranil (C 6 Cl 4 O 2 ) in chloroform at room temperature, with any ratio of the reactants leads to formation of [H 2 T(4‐X)PP(C 6 Cl 4 O 2 ) 2 ] compounds as a sole yield. The significant UV‐vis, 1 H NMR, and 13 C NMR spectral results suggested distortion of porphyrin core structure in the molecular complexes. Spectral data of the complexes revealed that the lone pair electron of a pyrrolenine nitrogen of porphyrin (σ‐electron donor) occupy π * orbital of a CO group in one o ‐chloranil molecule (π‐electron acceptor). J. Heterocyclic Chem., (2009).
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