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Tuning the tautomeric behavior of tris(salicylaldimines)
- Source :
- Org. Biomol. Chem.. 15:8418-8424
- Publication Year :
- 2017
- Publisher :
- Royal Society of Chemistry (RSC), 2017.
-
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.
- Subjects :
- Tris
Chemistry
Stereochemistry
Organic Chemistry
Substituent
Supramolecular chemistry
Electron delocalization
New materials
02 engineering and technology
010402 general chemistry
021001 nanoscience & nanotechnology
01 natural sciences
Biochemistry
Tautomer
Relative stability
0104 chemical sciences
3. Good health
chemistry.chemical_compound
Computational chemistry
Polar effect
Physical and Theoretical Chemistry
0210 nano-technology
Subjects
Details
- ISSN :
- 14770539 and 14770520
- Volume :
- 15
- Database :
- OpenAIRE
- Journal :
- Org. Biomol. Chem.
- Accession number :
- edsair.doi.dedup.....81e781e40203dd86f586f6bdf8e4ed76