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The NMR spectra of the porphyrins: 24 —The NMR spectra of some tetraarylchlorins
Author(s) -
Abraham Raymond J.,
Plant James E.,
Bedford Geoffrey R.
Publication year - 1983
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/omr.1270211207
Subject(s) - porphyrin , chlorin , chemistry , steric effects , ring (chemistry) , pyrrole , nmr spectra database , adduct , reagent , proton nmr , spectral line , carbon 13 nmr , zinc , stereochemistry , crystallography , photochemistry , organic chemistry , physics , astronomy
The synthesis and complete assignment of the 1 H NMR spectra of 5‐( o ‐pivaloylaminophenyl)‐10,15,20‐triphenylporphyrin (PIVTPP) and its two chiral dihydro adducts 3,4‐dihydro‐(PIVPTPC‐I)‐ and 7,8‐dihydr‐ (PIVPTPC‐II)‐porphyrins are reported. The use of the zinc complexes of the chlorins as chiral shift reagents with optically active bases is discussed. Comparison of the observed shift differences between the chlorins and the parent porphyrin with those calculated by a ring current model shows that a decrease in the ring current occurs on chlorin formation, and also specific effects occur at the reduced pyrrole ring, presumably reflecting different steric constraints.
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