Document Type


Date of Award



College of Science, Engineering, and Technology (COSET)

Degree Name

MS in Chemistry

First Advisor

Professor.John B. Sapp


The refined synthesis of 1,1 '-bis-(2-naphthol) sulfide and the syntheses of the related acetate, propionate and phenoxyacetate ester derivatives are reported with IR and NMR spectroscopic analysis and proton signal assignments. The synthesis of 1,1'-bis-(2-naphthol) sulfide is found to be more effective at an ambient temperature of O°C and possibly lower, not under reflux conditions as previously reported. The spectroscopic data strongly indicate that all four compounds were synthesized. The IR spectra showed a band at 3692.63 em" for the hydroxide moiety of 1,1 '-bis-(2-naphthol) sulfide and the typical carbonyl stretching band around 1700 em" for the esters. The FT-NMR data showed a competing influence between the alpha substituent, the sulfur atom, and the beta substituents on the magnetic character of protons 4,5,6 and 7. The NMR data also indicate that 1,1'bis-( 2-naphthol) sulfide and its derivatives are the species synthesized, not 3,3'-bis( 2-naphthol) sulfide and the related derivatives.