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Conformational analysis of novel monoaryl substituted protoporphyrins by 1D NOE, 2D NOESY and molecular modeling studies
Author(s) -
Robinsohn Adriana E.,
Buldain Graciela Y.,
Maier Marta S.
Publication year - 1997
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.5570340441
Subject(s) - chemistry , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , porphyrin , coplanarity , computational chemistry , photochemistry , geometry , mathematics
Porphyrins 1–4 are monoaryl protoporphyrins substituted on C‐5 or C‐15 by a phenyl group. One‐ and two‐dimensional nOe experiments and molecular modeling studies allowed us to find the most favorable conformations for these compounds. In the four porphyrins, the exocyclic phenyl group adopts a non‐coplanar disposition relative to the plane of the macrocycle and this is reflected in the ID nOe difference and 2D NOESY results. In porphyrins 1 and 3 the macrocycle is nearly planar while nonplanar saddle conformations were obtained for porphyrins 2 and 4.