Jump to main content
Jump to site search

Issue 39, 2017
Previous Article Next Article

Tuning the tautomeric behavior of tris(salicylaldimines)

Author affiliations

Abstract

Five new tris(N-salicylaldimine) (TSAN) analogues were prepared and characterized. NMR and single-crystal X-ray diffraction studies showed that they are found in different tautomeric forms, ranging from keto–enamine to enol–imine, with two showing intermediate behavior. We present a simple structural model governing the relative stability of the keto–enamine versus enol–imine tautomeric form of TSANs, based on experimental and theoretical findings on the new and existing TSAN analogues. Examination of electron delocalization throughout this range reveals a connection between tautomeric state and whether the substituent is σ or π electron withdrawing/donating. This can be used as a qualitative guide to design TSANs with controlled tautomeric behavior. These results will be helpful to the growing number of researchers in supramolecular chemistry who use TSANs to construct new materials and cages.

Graphical abstract: Tuning the tautomeric behavior of tris(salicylaldimines)

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Aug 2017, accepted on 19 Sep 2017 and first published on 27 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02058A
Citation: Org. Biomol. Chem., 2017,15, 8418-8424
  •   Request permissions

    Tuning the tautomeric behavior of tris(salicylaldimines)

    S. H. M. Mehr, H. Oshima, V. Carta, B. O. Patrick, N. G. White and M. J. MacLachlan, Org. Biomol. Chem., 2017, 15, 8418
    DOI: 10.1039/C7OB02058A

Search articles by author

Spotlight

Advertisements