Synthesis of new macrocyclic polyamides and polysulfonamides and a study of their complexation behavior using ¹H-NMR and mass spectrometry

Sleem, Hisham (2013) Synthesis of new macrocyclic polyamides and polysulfonamides and a study of their complexation behavior using ¹H-NMR and mass spectrometry. Doctoral (PhD) thesis, Memorial University of Newfoundland.

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Abstract

The reactions of isophthaloyl dichloride with "Jeffamine-176 and "Jeffamine-148" in the presence of triethylamine forms macrocyclic amide compounds. Also, the reaction of the chromotropic acid derivative with "Jeffamine-176" or with "Jeffamine-148" forms macrocyclic sulfonamides. The product ratios of these new macrocycles depend on the reaction conditions. The compounds have been found to be modest hosts for tetrabutylammonium and metal halides using ¹H NMR titration experiments. These experiments are described in Chapters 2 and 3. -- Their association constant (Kassoc) values were determined usmg isothermal nonlinear 1:1 binding curve fitting plots. Single-crystal X-ray structures for eight new compounds were obtained and confirmed the proposed structures. The photochemical behaviour of some of the chromotropic acid-based macrocyclic sulfonamides is also reported. -- The titration properties of the tetrabutylammonium halides (TBAX, X = C1, Br or I) alone with CDC1₃ using ¹H NMR chemical shift changes are described in Chapter 4. From the resulting titration curves a linear concentration-dependent relationship could be observed. A Single-crystal X-ray structure for TBABr:CH1₃C has been obtained.

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