In this thesis work, the results of microwave investigation and structural determination for benzonitrile and some of its fluorinated derivatives are presented. The pure rotational spectra of the studied compounds including benzonitrile, 2-fluorobenzonitrile, 3-fluorobenzonitrile, 2,3-difluorobenzonitrile, 2,4-difluorobenzonitrile and pentafluorobenzonitrile were investigated. Measuring the rotational spectra of the parent molecules and the minor 13C and 15N isotopic species allowed the derivation of the substitution and effective structures for these molecules. Using the effective and the calculated ab initio structures, the geometries of the fluorinated derivatives were compared to that of the reference compound (benzonitrile) and the effect of single, double and full fluorination on the geometry of benzonitrile was examined. The observed distortions in the BN geometry caused by single, double and full fluorination were interpreted by hybridization theory and intramolecular non-bonded interactions. / February 2015

Single crystal X-ray crystallography instructional materials were developed using a variety of compounds including sugar, Epsom salt, pyrite, copper(II) acetate, and rhodium(II) acetate. Rhodium(II) acetate was reacted with a variety of functionalized benzonitriles, and when crystals were obtained, characterized using single crystal X-ray crystallography. Rhodium(II) acetate with adducts of 4-nitrobenzonitrile and 4-(dimethylamino)benzonitrile were also characterized using proton NMR spectroscopy and Fourier Transform Infrared Spectroscopy. Rhodium(II) acetate with adducts of 4-(dimethylamino)benzonitrile was used as a catalyst in a proof-ofconcept reaction to determine if it acts as a catalyst in cyclopropanation reactions. Further, the new rhodium(II) acetate dinitrile compounds were investigated to determine if they would yield a different product ratio of cyclopropanes than that from the model Rh=CRR' mediated reaction between ethyl diazoacetate and styrene. The resulting cyclopropanation products were characterized using Gas Chromatography Mass Spectrometry. Preliminary experimental results yielded a trans- to cis-2-phenylcyclopropanecarboxylate ratio of 40:60.