Date of Award

8-7-2003

Degree Type

Thesis

Degree Name

M.S.

Degree Program

Chemistry

Department

Chemistry

Major Professor

Jursic, Branko

Second Advisor

Gibb, Bruce

Third Advisor

Wang, G.

Fourth Advisor

Wiley, John

Fifth Advisor

Trudell, Mark

Abstract

Through NMR experiments of the reaction of barbituric acid with carbodiimide, a general synthetic procedure for the preparation of 5-diaminomethylenebarbiturates (DABA) was developed. This procedure is very simple and applicable to the preparation of large quantities of DABA derivatives. Through the X-ray structural study of one of the DABA derivatives it was established that these compounds have a ylide-type structure with strong charge separation inside the molecule. 5-Ylide-pyridinium-methyl barbituric acid derivatives were investigated with the isolation of 4-dimethylamino-1-(2,4,6-trioxohexahydro- pyrimidin-5-ylide-methyl)-pyridinium as well as its corresponding 1,3- dimethylbarbituric acid derivative with quantitative yields. An alternative approach was attempted in order to prepare chiral 5-ylide-pyridinium-methyl-barbituric acid derivatives thus containing a chiral center between the charge separation. The extreme instability of the derivatives under investigation afforded the unique isolation of 4-dimethylamino-1- [(1,3-dimethyl-2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-phenyl-methyl]-pyridinium in quantitative yield.

Rights

The University of New Orleans and its agents retain the non-exclusive license to archive and make accessible this dissertation or thesis in whole or in part in all forms of media, now or hereafter known. The author retains all other ownership rights to the copyright of the thesis or dissertation.

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