The foci of this research are twofold. The experimental projects will focus on the investigating the physical and chemical properties of pyramidalized alkenes, obtaining photodetachment spectra of the radical anions of several of these molecules and of the radical anion of cyclobutadiene, and attempting to observe a derivative of cyclopentane-2-one-1,3-diyl in matrix isolation. The computational research will include studies of stereomutations of cyclopropane and geminally disubstituted derivatives, potential surfaces for several other types of organic reactions, geometries of and energy differences between electronic states of both di- and triradicals, substituent and solvent effects on C-H and O-H bond dissociation energies, strain in paddlanes and the differences between the chemistry of phenylnitrene and phenylcarbene. With this accomplishment based renewal award, the Synthetic Organic Program is supporting the research of Dr. Weston T. Borden of the Department of Chemistry at the University of Washington. Professor Borden will focus his work on the study of highly strained organic molecules. The combination of both experimental and theoretical methodology can offer new insights to the types of bonding that carbon can undergo.