Remarkable effect of hydrogen bonding between ring and axle components on deslipping reactions of rotaxanes

Keiji Hirose*, Yamato Nakamura, Hirokazu Takano, Keiji Nishihara, Yoshito Tobe

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A series of rotaxanes 1·5, 2·5, 3·5, and 4·5 bearing a different substituent (X = NO 2 , Br, H, and OMe, respectively) at para position on the phenol moiety of the ring component exhibit clear difference in deslipping behavior. The difference in the deslipping rates is consistent with the difference in intercomponent hydrogen bonding strength estimated from the O-H stretching vibration wavenumbers. The para substituent dictates the relative strength of the intra- and intermolecular hydrogen bonds. Thus the incorporation of an intramolecular hydrogen bond allows for tunability of the strength of the intercomponent interaction.

Original languageEnglish
Pages (from-to)3443-3445
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
StatePublished - 1 Jul 2009

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