DIASTEREOISOMERS IN SEDIMENTARY VANADYL PORPHYRINS

被引:12
作者
BOREHAM, CJ
CLEZY, PS
ROBERTSON, GB
机构
[1] UNIV NEW S WALES,DEPT ORGAN CHEM,KENSINGTON,NSW 2033,AUSTRALIA
[2] AUSTRALIAN NATL UNIV,RES SCH CHEM,CANBERRA,ACT 2601,AUSTRALIA
关键词
D O I
10.1021/ef00024a008
中图分类号
TE [石油、天然气工业]; TK [能源与动力工程];
学科分类号
0807 ; 0820 ;
摘要
The observation that the product of vanadyl insertion into the free-base porphyrin 15I-methyl-15, 17-propanoporphyrin separated into two near equal area peaks on HPLC analysis precipitated an investigation into the structure of both vanadyl porphyrins. Semipreparative HPLC and TLC were used to isolate pure components, and an X-ray structure determination on the more polar compound revealed a structure wherein the out-of-plane vanadyl and 15I-methyl groups were opposed, referred to as up-axial, relative to the plane of the porphyrin ring. The other complex is tentatively assigned to the diastereoisomer in which both groups are juxtaposed, down-axial. Metalloporphyrins in which the metal is coplanar with the ligand plane cannot have this diastereoisomerism. Sedimentary vanadyl porphyrins from the immature Serpiano oil shale contain both diastereoisomers but in a different ratio compared to the synthetic mixture. Artificial maturation experiments on the diastereoisomers suggest isomer interconversion can occur and the up-axial configuration is the more stable. © 1990, American Chemical Society. All rights reserved.
引用
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页码:661 / 664
页数:4
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