1. Sponsor: Professor Vince DeTuri, References from Professor Heinz Koch

2. Single Proton Nucleus N. Mass: 1.6726x10 -27 kg Lightest Element Proton (1.6726x10 -27 kg) Neutron (1.6749x10 -27 kg) Added Neutron N. Mass: 3.3475x10 -27 kg 200.13% more massive than Hydrogen Atom. Two added Neutrons N. Mass: 5.0224x10 -27 kg 300.28% more massive than Hydrogen Atom.

3. Experimental Observation: Reactions involving Hydrogen transfer go faster than Deuterium transfer, which is faster still than Tritium. Why? Energy Barrier Energy! Energy decides which particles can cross an activation barrier. Hydrogen requires the least amount of energy for transfer during a reaction. Hydrogen, deuterium, and tritium have different masses but behave the same electronically.

4. Energy Getting from point A to point B requires Energy. ΔE Deuterium sits lower in energy than Hydrogen, and Tritium sits lower still. H D T This means that Hydrogen requires the least ΔE to get over the energy barrier. The result is that Hydrogen will transfer the fastest, and these relative rates can be experimentally observed. B A Reaction Progress XH Y - (X H Y) - X - HY

5. Professor Heinz Koch began studying the reaction of certain alkenes with methoxide ion. The Alkene Benzyl-β,β-difluorostyrene - Hydrogen Carbon Fluorine Oxygen The Alkane Proton Transfer! Proton Transfer: Can study isotope effects… However: No isotope effects were observed! What is happening in this reaction? + (E) & (Z) Isomers Methoxide/Methanol

6. The reaction mechanism can be summarized with a theoretical energy diagram: The Alkene (E) & (Z) Isomers The Alkane - Carbanion H-Bonding Proton Transfer! Reversible Steps Describe Internal Proton Return! Our Current Research Involves an in-depth computational analysis of steps (B), (D), and (E). Energy

7. Organic Chemistry: Make Unexpected Observations Cannot observe proton, deuteron, and trition transfer during reactions! Can determine kinetic isotope effects through chemical kinetics. Physical Chemistry: Model Unexpected Observations Cannot easily determine reaction rates and kinetic isotope effects. Can observe reaction pathways, intermediates, product analysis, and relative energetics! Reaction Progress Energy

8. Reaction Progress Energy Interested only in proton exchange right now. Too Difficult to Calculate! B A C Chloroform Using b3lyp/6-31g+(d,p) level of theory for optimization to support energy diagram. Calculate the Optimization Energies of:

9. Transition State? MethoxideChloroform 15 Days, 7 Hours, 35 Minutes, 17 Seconds

10. Energy Calculations E Encounter Complex Transition State Hydrogen Bound 0 kJ/mol 14 kJ/mol 30 kJ/mol (approx) Many TS calculations crashed; many approximations were made. Key to understanding proton exchange.

11. Find an accurate Transition State. Does the TS connect the EC and HB? Build up the solvent system. Four Solvating methanol molecules… Use solvent wrapping technique. Try different solvents. Try different carbanion systems. Model the actual system. Pentafluorobenzene 9-Methyl-Fluorene

12. Sponsor: Professor Vince DeTuri, References from Professor Heinz Koch