The synthesis of a pyridine-: N -oxide isophthalamide rotaxane utilizing supplementary amide hydrogen bond interactions

Evans, Nicholas Henley and Gell, Charlie and Peach, Michael Joseph George (2016) The synthesis of a pyridine-: N -oxide isophthalamide rotaxane utilizing supplementary amide hydrogen bond interactions. Organic and Biomolecular Chemistry, 14 (33). pp. 7972-7981. ISSN 1477-0520

Preview

PDF (Evans Gell Peach OBC 2016 for PURE.docx)
Evans_Gell_Peach_OBC_2016_for_PURE.docx.pdf - Accepted Version
Available under License Creative Commons Attribution-NonCommercial.
Download (1MB)

Preview

PDF (c6ob01435f (1))
c6ob01435f_1_.pdf - Published Version
Available under License Creative Commons Attribution.
Download (2MB)

Abstract

The synthesis of a pyridine-N-oxide containing rotaxane, not requiring an additional ionic template, has been achieved in 32% yield. Successful rotaxane formation is dependent upon the structure of the isophthalamide macrocycle used, an observation which has been rationalised by a combination of NMR spectroscopy, X-ray crystallography and computational modelling.