SIR Chemistry Investigation Abstract
DESIGN AND SYNTHESIS OF NOVEL MACROMOLECULAR PERAZA-CRYPTAND AND THE SEARCH FOR DIHYDROGEN BONDING IN H6PERAZA[2.2.2]CRYPTAND•NABH4
Presenter:
MengFei S. Yin, Illinois Mathematics and Science Academy
Advisor:
Dr. James E. Jackson, Michigan State University
Abstract:
This study aims to develop a method for the large-scale synthesis of a novel, easy to handle peraza-cryptand, based on common inexpensive reagents. The process involves tetrapode capping that links four molecules of ethylenediamine to two molecules of ethylenediaminetetraacetic acid (EDTA). The proposed cryptand may be useful in forming stable complexes with alkali metal cations and enable the preparation of new, perhaps even more stable, electrides or alkalides. In protonated form, the cryptand may also be capable of binding anions such as halides or hydroxide. During the synthesis process, we found that when the reaction was performed with an excess of ethylenediamine, the tetramethyl ester of ethylenediaminetetraacetic acid reacts with four equivalents of ethylenediamine to form the tetrakis(N-2-aminoethyl) tetraamide of EDTA. The product was isolated via crystallization in the presence of drying agent NaOH and was produced in 8.82% yield with no impurities other than excess ethylenediamine. In this investigation, we also searched for the existence of dihydrogen bonding between the amine proton and the borohydride hydride in H6Peraza[2.2.2]cryptand•NaBH4 using powder x-ray diffraction, x-ray crystallography, IR spectroscopy, 1H NMR, and NOESY. The likelihood of dihydrogen bonding was shown to be very high, but an aprotic solvent that dissolves H6Peraza[2.2.2]cryptand•NaBH4 relatively well is still needed in order to find concrete evidence of dihydrogen bonding.