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Front Cover: Two‐step Conformational Control of a Dibenzo Diazacyclooctane Derivative by Stepwise Protonation (Asian J. Org. Chem. 6/2021)
Author(s) -
Ishiwari Fumitaka,
Miyake Sayuri,
Inoue Keiki,
Hirose Keiji,
Fukushima Takanori,
Saeki Akinori
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100237
Subject(s) - chemistry , protonation , derivative (finance) , proton , crystallography , stereochemistry , ion , organic chemistry , financial economics , economics , physics , quantum mechanics
Dibenzo‐1,5‐diazacyclooctane (DACO) derivative undergoes two‐step protonation and would be useful for developing multistep stimuli‐responsive systems. The first proton (the brown cat) affords a proton‐bridged Tröger's‐base‐like pseudo bicyclic structure, and the second proton (the blue and white cats) causes an electrostatic repulsion between positively charged nitrogen atoms, as if the blue and white cats pull the two nitrogen atoms apart, to afford a deformed boat‐shape eight membered ring structure. As a result, the degree of bending and conformational rigidity of the DACO become higher as the degree of the protonation is increased. More information can be found in the Communication by Fumitaka Ishiwari et al.