Towards the Synthesis of (NAPY1): A Potential Metal-Peroxide Binding Ligand

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Title: Towards the Synthesis of (NAPY1): A Potential Metal-Peroxide Binding Ligand
Author: Nwaneshiudu, Ikechukwu
Advisor: Scarrow, Robert C.
Department: Haverford College. Department of Chemistry
Type: Thesis (B.S.)
Issue Date: 2007
Abstract: We report the design and the first synthetic step towards the synthesis of a potential metal-peroxide binding ligand containing N,N-naphthyridone groups. We propose that these groups will be effective at coordinating to metals as well as also potentially binding and activating O2 because of the two possible sites on each pyridine ring for metal coordination and hydrogen bonding. The synthesis of the naphthyridine group is still in working progress, although the first intermidiate molecule was successfully synthesized and characterized. Studies of possible tautomers, using PC Spartan Pro, were performed to elucidate the most energetically favorable tautomer of the 7-methyl-1, 8- naphthyridine-2-one molecule. Our Semi-Empirical AM1 data showed the A, B, and C tautomers of the molecule having energies of 131.41 kJ/mol, 42.08 kJ/mol, and 79.15 kJ/mol respectively. Tautomer B being the molecule with the lowest conformational energy makes it the most enegetically favorable and stable tautomer of the three. Data from Hartree Fock 3-21G calculations also support this trend with energy differences of a least 10 kJ/mol for the A and C tautomers when compared the the tautomer B. Since, tautomer B is the desired molecule for the proposed ligand system, we have more inspiration to complete the synthesis of the naphthyridine group.
Subject: Naphthyridines -- Synthesis
Subject: Tautomerism
Subject: Ligand binding (Biochemistry)
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Nwaneshiudu, Ikechukwu. "Towards the Synthesis of (NAPY1): A Potential Metal-Peroxide Binding Ligand". 2007. Available electronically from

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