Evaluation of the Steric Bulk of Substituents Utilizing the Shuttling Behavior of [2]Rotaxanes with N‐Arylpyrrole Moieties. Issue 21 (4th December 2018)

• Record Type: Journal Article
• Authors: Yamashita, Yoshiaki; Saito, Yuuki; Kikkawa, Shoko; Mutoh, Yuichiro; Hosoya, Shoichi; Azumaya, Isao; Saito, Shinichi
• Other Names: Sauvage Jean‐Pierre guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 21(2019)
• Page Start: 3412
• Page End: 3420
• Publication Date: 2018-12-04
• Subjects: Macrocycles -- NMR spectroscopy -- Rotaxanes -- Steric hindrance -- Supramolecular chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801476
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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 results were compared with the data reported by other methods.