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Issue 39, 2017
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Tuning the tautomeric behavior of tris(salicylaldimines)

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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)

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Article information

18 Aug 2017
19 Sep 2017
First published
27 Sep 2017

Org. Biomol. Chem., 2017,15, 8418-8424
Article type

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

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