I. Addressing the Regioselectivity Problem in Organic Synthesis.II. A-B-A-B-A Block Amphiphiles. Balance between Hydrophilic andHydrophobic Segmentation. Open Access

Abstract

Part I. Addressing the Regioselectivity Problem in Organic Synthesis

A family of compounds with two nearly identical ketals on each has been synthesized in an effort to address the regioselectivity problem. A screening process uncovered a heterogeneous catalytic system that hydrolyzes one of two nearly identical ketals with a high selectivity.

Part II. A-B-A-B-A Block Amphiphiles. Balance between Hydrophilic and Hydrophobic Segmentation

Six penta-block amphiphiles of the general structure A-B-A-B-A or B-A-B- A-B (where A = a hydrophilic ether and B = a hydrophobic carbon chain) were synthesized and examined via water solubilities, surface activities, cloud points, and self-diffusion coefficients. It was found that segmentation can have a dramatic effect upon solute properties, including solubility, propensity to self- assemble, aggregation number, and cooperativity. These data are relevant to biological systems where segmentation is a widespread phenomenon.

Table of Contents

Table of Contents Part I. Addressing the Regioselectivity Problem in Organic Synthesis Page Introduction 2 Syntheses 11 Results and Discussion 19 A. Monitoring method by HPLC 19 B. Screening Process and Results 22 C. Discussion 30 D. Future Work 33 Conclusion 35 Experimental 36 A. HPLC monitoring 36 B. Synthesis 37 Footnotes and References - Part I 62 Part II. A-B-A-B-A Block Amphiphiles. Balance between Hydrophilic and Hydrophobic Segmentation Page Introduction 68 Syntheses 74 Characterization 78 A. Solubility 78 B. Surface tension, critical micelle concentration (CMC), and interfacial area per molecule 79 C. Cloud point 87 D. Aggregation by NMR diffusion 89 Conclusion 94 Experimental 95 A. Syntheses of E m C n E m C n E m 95 B. NMR Diffusion Experiments 106 Footnotes and References - Part II 108

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School	Laney Graduate School
Department	Chemistry
Degree	PhD
Submission	Dissertation
Language	English
Research Field	Chemistry, Organic
Keyword	regioselectivity, enzyme, block amphiphile
Committee Chair / Thesis Advisor	Menger, Fred M, Emory University
Committee Members	Liebeskind, Lanny S, Emory University Blakey, Simon, Emory University

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