Thursday, 17 May 2007
3rd Floor Hall (Pfahler Hall)
272

Synthesis of a Potential Molecular Indicator: N-Azuleneiminodiacetic Acid

Peter F. Slivka and Carl Salter. Moravian College, Bethlehem, PA

Azulene (1) is an aromatic hydrocarbon with the same molecular formula as naphthalene, but unlike the colorless naphthalene, azulene has a brilliant royal blue color. The color of azulene changes dramatically when the ring system is substituted, and when it is exposed to strong acids. With a series of reactions, we intend to transform azulene into a chelating agent. Hopefully, the coordination complexes that N-azuleneiminodiacetic acid (4) forms with various metals ions will produce a variety of colors. Our synthesis involves nitrating 1 with tetranitomethane (TNM) to form 2, reduction of �NO2 to �NH2 3, and SN2 addition of chloroacetic acid 4. The first two intermediates (2,3) have been identified using UV-Vis spectroscopy and 1H-NMR spectroscopy. Further work is required to purify the final product.



Web Page: www.cs.moravian.edu/~csalter/aada.html

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