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Investigation of Electronic Effects of SN2 Reactions towards the Synthesis of Thiochromones

Undergraduate #86
Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)
Session: 1
Room: Exhibit Hall

Mina Perez - Winston-Salem State University
Co-Author(s): Alex Chavez, Winston-Salem State University, Winston-Salem, NC; Holden Hankerson, Winston-Salem State University, Winston-Salem, NC; and Dr. Fenghai Guo, Winston-Salem State University, Winston-Salem, NC.



Heterocycles including surfur-containing heterocycles are important class of molecules due to their rich biological actitivies. Aryl thiols have been shown to be important building blocks for the synthesis of sulfur-containing natural products and pharmaceutically active compounds. This research is focused on the synthesis of 3-aryl(thio)-propanoic acids from aryl thiols via SN2 reactions. 3-Aryl(thio)-propanoic acids are important intermediates for S-heterocycles synthesis. The hypothesis is that the electronic withdrawing and donating group on the aromatic ring will affect the reactivity of aryl thiols in SN2 reaction and thus the chemical yields. The scope of aryl thiols will be explored. The results on various electron-donating and electron-withdrawing groups will be presented. The exciting synthetic applications of 3-aryl(thio)-propanoic acids to the synthesis of thiochromones will also be presented.

Funder Acknowledgement(s): I would like to acknowledge NSF HBCU-UP 1831339.

Faculty Advisor: Fenghai Guo, guof@wssu.edu

Role: I developed SN2 reactions of aryl thiols. Initially started with thiolphenol to determine the optimal reaction condition. Explored the scope of aryl thiols and investigated electronic effects on the chemical yield. This includes setting up the reactions, monitoring the reactions, and purifying the compounds by column chromatography to determine the chemical yield.

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This material is based upon work supported by the National Science Foundation (NSF) under Grant No. DUE-1930047. Any opinions, findings, interpretations, conclusions or recommendations expressed in this material are those of its authors and do not represent the views of the AAAS Board of Directors, the Council of AAAS, AAAS’ membership or the National Science Foundation.

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