Structural and Aromaticity Control of [34]Octaphyrin(1.1.1.0.1.1.1.0) by Protonation and Deprotonation | Zendy

Naoda Koji | Zendy; Osuka Atsuhiro | Zendy

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Structural and Aromaticity Control of [34]Octaphyrin(1.1.1.0.1.1.1.0) by Protonation and Deprotonation

Author(s) -

Naoda Koji,

Osuka Atsuhiro

Publication year - 2017

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.201700144

Subject(s) - deprotonation , protonation , chemistry , aromaticity , medicinal chemistry , methanesulfonic acid , stereochemistry , computational chemistry , organic chemistry , molecule , ion

The structural and aromaticity control of hexakis(pentafluorophenyl) [34]octaphyrin(1.1.1.0.1.1.1.0) 1 was examined by protonation and deprotonation. Protonation of 1 with methanesulfonic acid (MSA) induced a structural change from a figure‐eight to a rectangular shape, accompanied by an aromaticity change from nonaromatic to strong Hückel aromatic. Deprotonation of 1 with tetrabutylammonium difluorotriphenylsilicate (TBAT) or fluoride (TBAF) produced a mono‐deprotonated species with a similar figure‐eight conformation and nonaromaticity.

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