Graduate Thesis Or Dissertation
 

Synthesis, characterization, and analysis of nitroaromatic compounds

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  • Nitroaromatic compounds have important chemical applications and can be found in nature as pollution sources. Synthetic nitroaromatic compounds have been used in a variety of materials including explosives, pharmaceuticals, dyes, plastics, and pesticides. These compounds can find their way into the environment through normal or improper disposal methods. Poly-aromatic compounds are important structural motifs due to their presence in complex natural products and pharmaceutical scaffolds. Previously, the Carter laboratory has developed a Diels-Alder Approach to Biaryls (DAB), which provides access to highly functionalized poly-aromatic compounds. The extension of this methodology to the synthesis of heterocycles such as poly-aromatic triazoles and isoxazoles through the use of a [3+2] dipolar cycloaddition utilizing o-nitrophenylalkynes will be disclosed. Nitro-polycyclic aromatic hydrocarbons (NPAHs) are potential carcinogenic compounds found in the atmosphere. NPAHs can be formed as byproducts of the incomplete combustion of coal, crude oil, gas, tobacco, and other organic substances. NPAHs are also formed from the reaction of the parent PAHs with atmospheric oxidants. Due to the harmful nature of PAHs it is important to investigate the properties of the derivatized versions of these pollutants. The lack of significant quantities of NPAH’s for full characterization, toxicology studies, and use as analytical standards have motivated our efforts toward the synthesis and analysis of these compounds. The direct nitration of benzo[k]fluoranthene (BKF) and benzo[ghi]perylene (BGHIP) provided separable mixtures of regioisomers. The regiochemistry and full characterization of the isolated nitrated compounds was confirmed through a variety of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic techniques, infrared (IR) spectroscopy, high-resolution mass spectroscopy (HRMS), and gas chromatography mass spectroscopy (GC-MS). Prep HPLC on isolated compounds provided 99% pure samples as shown by GC-MS. These samples were submitted for Ames testing. A generalized method to access nitrated BKF derivatives employs palladium cross-coupling reactions to bring together strategically designed naphthalene components.
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Déclaration de droits
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