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X‐ray Structures of a Phenanthroline‐Strapped Porphyrin and Its Dihydrated Zinc(II) Complex: Convergent Distal Hydrogen Bonds and “CH ··· O” Interactions
Author(s) -
Ochsenbein Philippe,
Bonin Michel,
Schenk Kurt,
Froidevaux Jérôme,
Wytko Jennifer,
Graf Ernest,
Weiss Jean
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199907)1999:7<1175::aid-ejic1175>3.0.co;2-b
Subject(s) - chemistry , zinc , crystallography , hydrogen bond , porphyrin , phenanthroline , moiety , molecule , water of crystallization , free base , ligand (biochemistry) , stereochemistry , crystallization , metal , crystal structure , photochemistry , inorganic chemistry , organic chemistry , salt (chemistry) , biochemistry , receptor
Abstract The X‐ray structure of a phenanthroline‐(phen‐)strapped 1,10‐diphenylporphyrin 1 has been resolved. From the structure obtained, it is apparent that in spite of the rigidity of the strap the porphyrin ring is only slightly distorted, and that the substituents on the phen moiety define what would seem to be a hydrophobic pocket. Metallation of the free base 1 with zinc(II) acetate yields a metallic complex ( 1 )Zn with a free axial coordination site. Crystallization of the zinc complex in the presence of a hindered base ( N ‐methylimidazole, denoted N ‐MeIm) in organic solvents affords single crystals of a porphyrinatozinc(II) species, in which two water molecules are surprisingly present in the encumbered (distal) pocket of the phen site. One water molecule is axially bound to the zinc(II) ion, while the other is doubly hydrogen‐bonded, as an H‐bond donor to the phenanthroline and as an H‐bond acceptor to the axial water ligand.