Event Title

Synthesis of “Thiocrown 12” for the Stabilization of Cu+ in Titration Experiments

Poster Number

53

Faculty Mentor

Dr. Nicholas Grossoehme & Dr. Jay Hanna

College

College of Arts and Sciences

Department

Chemistry, Physics and Geology

Location

Richardson Ballroom

Start Date

22-4-2016 2:15 PM

End Date

22-4-2016 4:15 PM

Description

Isothermal Titration Calorimetry (ITC) is an ideal method to study binding reactions independently of spectral signatures. The biologically relevant oxidation state of copper, copper (I), is one such “spectroscopically silent” ion. Unlike traditional methods, ITC relies on the generation of a heat signature; as such, it is readily used to quantify thermodynamic properties of Cu+ binding reactions. However, this metal is difficult to study under aqueous conditions due to its sensitivity to oxygen and disproportionation to Cu2+ and Cu0. This project aims to use a cyclical tetrathioether, “thiocrown 12,” for the delivery of chemically stable cuprous ions to systems of interest. The thiocrown synthesized is desirable due to the four coordinate tetrahedral geometry that the cavity presents. Recognition of these qualities led this research to continue in the synthesis of the thiocrown. Through the reaction of “dibromopropanediol 3” with Na2S the cyclized “thietane 9” product was obtained in high yield and purity. The product was confirmed by Gas Chromatography Mass Spectrometry (GC Mass Spec) and comparison to literature 1H-NMR. “Diiodide 10” was produced by reacting “thietane 9” with diiodopropane; however, the literature conditions for this reaction were unusable. To get around this, a system was optimized for the microwave synthesis of “diiodide 10,” significantly dampening the time needed for the synthesis. The most effective conditions were found to be 135oC for 10 hours.

Previously Presented/Performed?

Summer Undergraduate Research Experience (SURE) Symposium, Winthrop University, July 2015

Grant Support?

Supported by grants from the National Institutes of Health IDeA Networks for Biomedical Research Excellence (NIH INBRE) and the Winthrop University Research Council

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Apr 22nd, 2:15 PM Apr 22nd, 4:15 PM

Synthesis of “Thiocrown 12” for the Stabilization of Cu+ in Titration Experiments

Richardson Ballroom

Isothermal Titration Calorimetry (ITC) is an ideal method to study binding reactions independently of spectral signatures. The biologically relevant oxidation state of copper, copper (I), is one such “spectroscopically silent” ion. Unlike traditional methods, ITC relies on the generation of a heat signature; as such, it is readily used to quantify thermodynamic properties of Cu+ binding reactions. However, this metal is difficult to study under aqueous conditions due to its sensitivity to oxygen and disproportionation to Cu2+ and Cu0. This project aims to use a cyclical tetrathioether, “thiocrown 12,” for the delivery of chemically stable cuprous ions to systems of interest. The thiocrown synthesized is desirable due to the four coordinate tetrahedral geometry that the cavity presents. Recognition of these qualities led this research to continue in the synthesis of the thiocrown. Through the reaction of “dibromopropanediol 3” with Na2S the cyclized “thietane 9” product was obtained in high yield and purity. The product was confirmed by Gas Chromatography Mass Spectrometry (GC Mass Spec) and comparison to literature 1H-NMR. “Diiodide 10” was produced by reacting “thietane 9” with diiodopropane; however, the literature conditions for this reaction were unusable. To get around this, a system was optimized for the microwave synthesis of “diiodide 10,” significantly dampening the time needed for the synthesis. The most effective conditions were found to be 135oC for 10 hours.