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Porphyrins of Serpiano shale: Structures and origins

Conference · · Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States)
OSTI ID:5669768
A prerequisite for understanding the origins and degradative pathways of sedimentary alkyl porphyrins is full structural characterization of individual components of such complex mixtures. Thus, the structures of a number of porphyrins from the Serpiano oil shale (Triassic, Monte San Giorgio, Switzerland) have been investigated, acetylation being applied in the separation of components containing unsubstituted ..beta..-positions. HPLC of demetallated fractions has allowed isolation of a number of components, mainly containing an exocyclic alkano ring. The structures (as the zinc (II) complexes) were studied by proton NMR, using selective decoupling and nuclear Overhauser effect (n.O.e.) studies, and by mass spectrometry under chemical ionization conditions using H/sub 2/ as reagent gas. Such an approach afforded the full assignment of a variety of structures, including components with a five, a methyl-substituted size or a seven membered exocyclic ring. In addition, the structure of a widely occurring mono-unsubstituted C/sub 30/ aetioporphyrin has been established fully. The number of Serpiano porphyrins characterized extends the known series of isomeric types, and their structures have been rationalized in terms of geochemical alteration of known chlorophylls. The individual components have also been used as standards in applied studies of sedimentary porphyrin distributions using HPLC and GC-MS co-chromatography.
Research Organization:
School of Chemistry, Univ. of Bristol, Bristol BS8 1TS
OSTI ID:
5669768
Report Number(s):
CONF-860425-
Conference Information:
Journal Name: Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States) Journal Volume: 31:2
Country of Publication:
United States
Language:
English