In this project in the Organic Dynamics Program, Professor Richard H. Smith at Western Maryland College will study "Triazoline Hydrolysis: The Chemistry of Cyclic Triazenes". Triazenes are a family of organic compounds whose key structural feature is a chain of three consecutive nitrogen atoms. Triazenes and their related derivatives are of interest as important substrates for physical organic chemical and pharmacological studies. The results of these studies will afford a better understanding of the mechanisms of triazene metabolism and degradation in cellular systems. The hydrolysis of triazolines, a general model for cyclic triazenes, is being studied and compared mechanistically to the corresponding reaction of acyclic triazenes. The mechanism of the hydrolytic decomposition of triazolines is being systematically explored through kinetic, product, and structure-reactivity experiments. A new reaction, the cyclization of 2-haloethyltriazenes leading to the formation of triazolines, is also being explored through kinetic and product studies. This reaction leads to new classes of compounds which include tetrahydro-1,2,3-triazines and tetrahydro-1,2,3-triazepines.