期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 1, 页码 233-239出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo061951j
关键词
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资金
- NIGMS NIH HHS [R01 GM049725-06, R01 GM049725, R01 GM049725-05, R01 GM049725-07, GM 49725] Funding Source: Medline
Porphyrins are stable molecules with a macrocyclic conjugated system and often peripheral substituents. This unique structure makes the electronic properties of the four meso-carbons (the methine bridges) nearly identical. Replacement of the weakly electron-polarizing 2,4-vinyl groups of protoporphyrin IX with strongly electron-polarizing acetyl groups not only leads to much lower meso-carbon reactivities toward electrophilic aromatic substitution but also results in a significant meso-selectivity (the beta- and gamma-meso-positions become much more nucleophilic (basic) than the alpha- and delta-meso-positions). To further investigate the relationship between the porphyrin meso-carbon reactivities and the peripheral substituents, two monoacetylporphyrin analogues also were synthesized. This investigation not only leads to empirical rules for predicting porphyrin meso-carbon selectivities but also provides important models for theoretical calculations of porphyrin aromaticity.
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