1. Progress Towards the Synthesis and Characterization of a Copper(I)-Phenyl Complex Thabiso Kunene; Thora Maltais (‘09), Mark Ziffer (’11), Rebecca Conry Department of Chemistry, Colby College, Waterville, ME, USA A complex consists of a central metal, bonded to a surrounding group of molecules or atoms called ligands. The ligands often bind the metal through atoms such as carbon, oxygen, or nitrogen. Numerous complexes occur naturally, for instance hemocyanins, which are proteins that carry oxygen in the bodies of some invertebrate animals such as lobsters. Organometallic complexes have metal-carbon bonds Organometallic complexes of copper are some of the most widely used reagents in synthetic organic chemistry, such as for adding an alkyl group to an acid chloride. However, most organocopper complexes are formed and used without being isolated so their chemistry is underdeveloped, including that for copper-arene complexes. Only a few copper(I)-arene complexes have been reported, for most of these, the copper(I) ion only interacts with the arene in the solid state, not in solution. We are continuing previous work in which the first Cu(I)-naphthyl complex (Figure 1) was synthesized, isolated, and shown to bind the arene group both in solution and in the solid state. This project aims to synthesize and characterize a Cu(I)-phenyl complex in order to probe the factors that contribute to the strength and selectivity of the copper-phenyl bond. The target complex (Figure 2) requires five synthetic steps, four to make the ligand plus another to make the complex. Compound 1 is formed by substituting the three Hs in diethanolamine with Ts from p-toluenesulfonic acid (TsCl). The resultant OTs is a better leaving group than OH to aid the synthesis of compound 2 in step 2. Compounds 1, 2, and 3 have been synthesized Our manipulative, analytical, chemical reasoning skills and understanding has greatly improved through handling and preparation of these compounds. Upon synthesis of the Cu(I)-phenyl complex, nuclear magnetic resonance (NMR) will be used to study the Cu(I)-phenyl binding ability and binding location. An attempt to grow crystals of the Cu(I)-phenyl complex will be made so that X-ray crystallography can be used to study the Cu(I)-phenyl binding in the solid state. The results will then be compared with those from Max Cushner’s work in order to better understand Cu(I)-arene complexes. 1.Conry, R. R.; Striejewske, W. S.; Tipton, A. A. Inorganic Chemistry 1999, 38, 2833-2843 2.Conry, R. R.; Tipton, A. A.; Striejewske, W. S.; Erkizia, E.; Malwitz, M. A.; Caffaratti, A.; Natkin, J. A. Organometallics 2004, 23, 5210 3.Chandrasekar, S.; McAuley, A. Inorganic. Chemistry. 1992, 31, 2234-2240 Colby College and Colby College Science Division Thora Maltais (‘09), Mark Ziffer (‘11), and Alex Tipton for previous results Max Cushner ACS-PRF Compound 3 is formed upon exchanging the Ts group with H, so that the H can be replaced with an ethyl phenyl arm in step 4. The cyclic compound 2 is made by replacing the OTs groups with the sulfur groups from 1,3-propanedithiol to form a ring. MATERIALS and METHODS This step adds the ethyl phenyl arm Benzene copper triflate will be used as a source of Cu(I) to try to form the target Cu(I)-phenyl complex labeled 5 below. Note: Even though a binding Cu-arene site is indicated, it has not yet been definitely determined. Ligand synthesis step 1 INTRODUCTION Ligand synthesis step 2 Ligand synthesis step 3 Ligand synthesis step 4 RESULTS and FUTURE DIRECTIONS Synthesis of complex CITATIONSACKNOWLEDGEMENTS