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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Osuka, Atsuhiro Yoshida, Kota Copley, Graeme Mori, Hirotaka |
| Description | Author Affiliation: Yoshida K ( Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970.) |
| Abstract | $A_{2}B-type$ B-methoxy subporphyrins 3 a–g and B-phenyl subporphyrins 7 a–c,e,g bearing meso-(2-substituted)aryl substituents are synthesized, and their rotational dynamics are examined through variable-temperature (VT) $^{1}H NMR$ spectroscopy. In these subporphyrins, the rotation of meso-aryl substituents is hindered by a rationally installed 2-substituent. The rotational barriers determined are considerably smaller than those reported previously for porphyrins. Comparison of the rotation activation parameters reveals a variable contribution of $ΔH^{≠}$ and $ΔS^{≠}$ in $ΔG^{≠}.$ 2-Methyl and 2-ethyl groups of the meso-aryl substituents in subporphyrins 3 e, 3 f, and 7 e induce larger rotational barriers than 2-alkoxyl substituents. The rotational barriers of 3 g and 7 g are reduced by the presence of the 4-dibenzylamino group owing to its ability to stabilize the coplanar rotation transition state electronically. The smaller rotational barriers found for B-phenyl subporphyrins than for B-methoxy subporphyrins indicate a negligible contribution of $S_{N}1-type$ heterolysis in the rotation of meso-aryl substituents. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 32 |
| Volume Number | 20 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2014-08-04 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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