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Evaluation of the Steric Bulk of Substituents Utilizing the Shuttling Behavior of [2]Rotaxanes with N ‐Arylpyrrole Moieties
Author(s) -
Yamashita Yoshiaki,
Saito Yuuki,
Kikkawa Shoko,
Mutoh Yuichiro,
Hosoya Shoichi,
Azumaya Isao,
Saito Shinichi
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801476
Subject(s) - steric effects , chemistry , electronic effect , rigidity (electromagnetism) , computational chemistry , stereochemistry , photochemistry , structural engineering , engineering
The activation energies of the shuttling of [2]rotaxanes with various N ‐arylpyrrole moieties were determined by variable temperature (VT) 1 H NMR experiments. The value provided a new quantitative scale for the estimation of the steric bulk of the substituents. The rigidity and the electronic effect of the substituents, which could inadequately influence the estimation of the steric bulk, were minimized in the method we presented.