Presentation Title

Improved synthesis of amino acid based imidazolium salts

Faculty Mentor

Jennifer Young

Start Date

18-11-2017 2:15 PM

End Date

18-11-2017 3:15 PM

Location

BSC-Ursa Minor 36

Session

Poster 3

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Metals, specifically silver and copper, have demonstrated antiviral and antibacterial properties. However, these metals cannot be ingested in their pure form because human bodies will reject them, so their medicinal applications are limited. Current research is being done to bind these metals to various types of ligands to enhance the biocompatibility of the metals. The focus of this project is to synthesize a series of amino acid based imidazolium salts that can be deprotonated to form pincer ligands for binding to cobalt, copper, and nickel. A synthesis for glycine imidazolium salt (GIS) can be found in the literature, but the synthesis results in low yields. The purpose of this project was to find a better synthesis for the glycine imidazolium salt, and to attempt to make other imidazolium salts with different amino acids with higher yields. A more efficient method was found using acetic acid as a catalyst. The percent yield of GIS with the first method was 13.7%, and with the improved method, the percent yield was 45.8%. Using this method, the alanine imidazolium salt was also synthesized. Proton NMR spectroscopy was used to verify the formation of the desired products and their purity. Future work will include attempting to make imidazolium salts with different amino acids, such as methionine and using these ligands to react with first-row transition metals.

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Nov 18th, 2:15 PM Nov 18th, 3:15 PM

Improved synthesis of amino acid based imidazolium salts

BSC-Ursa Minor 36

Metals, specifically silver and copper, have demonstrated antiviral and antibacterial properties. However, these metals cannot be ingested in their pure form because human bodies will reject them, so their medicinal applications are limited. Current research is being done to bind these metals to various types of ligands to enhance the biocompatibility of the metals. The focus of this project is to synthesize a series of amino acid based imidazolium salts that can be deprotonated to form pincer ligands for binding to cobalt, copper, and nickel. A synthesis for glycine imidazolium salt (GIS) can be found in the literature, but the synthesis results in low yields. The purpose of this project was to find a better synthesis for the glycine imidazolium salt, and to attempt to make other imidazolium salts with different amino acids with higher yields. A more efficient method was found using acetic acid as a catalyst. The percent yield of GIS with the first method was 13.7%, and with the improved method, the percent yield was 45.8%. Using this method, the alanine imidazolium salt was also synthesized. Proton NMR spectroscopy was used to verify the formation of the desired products and their purity. Future work will include attempting to make imidazolium salts with different amino acids, such as methionine and using these ligands to react with first-row transition metals.