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MO Calculations of Imine Hydrolysis and Cu Complex Formation.

MO Calculations of Imine Hydrolysis and Cu Complex Formation. CHM 6440/7440 Winter 2005 By Rabab Aoun. Outline. Introduction My Project Reaction Mechanism MO Calculations and reaction energy Substituents Effect. Introduction.

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MO Calculations of Imine Hydrolysis and Cu Complex Formation.

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  1. MO Calculations of Imine Hydrolysis and Cu Complex Formation. CHM 6440/7440 Winter 2005 By Rabab Aoun

  2. Outline • Introduction • My Project • Reaction • Mechanism • MO Calculations and reaction energy • Substituents Effect

  3. Introduction • Many studies on the hydrolysis of imines in the presence of , and . • Alkaline hydrolysis of the imine anion involves intermolecular general base catalysis. • The effect of stabilizing the aldimine linkage to hydrolytic splitting is maximum for . • Generation of complexed phenoxyl-containing species depends on the presence of substituents at the ortho and para positions of the phenolate ring.

  4. My Project • Hydrolysis of imine in the presence of . • Imine hydrolysis by triethylamine and water. • Computational studies investigating all the parts of the reaction.

  5. Imine Hydrolysis Reaction + Pyridine t-butyl Phenol HBPIE

  6. Cu Complex Reaction Cu Complex Reaction + + 2 2

  7. Mechanism of Hydrolysis

  8. Mechanism of Hydrolysis

  9. MO Calculations • Standard ab initio molecular orbital calculations are performed at B3LYP/ 6-31G(d) • Optimization and frequency method calculation • Collection of electronic energy and zero point correction.

  10. MO Calculations of Imine Hydrolysis

  11. MO Calculations of Cu complex

  12. Cu Monomer and its Radical

  13. t-butyl Phenol and its Radical

  14. Substituent’s Effect on Phenoxyl Complexes • The generation of complexed phenoxyl-containing species depends on the presence of substituents at the ortho and para positions of the phenolate ring. • Unsubstituted phenolates are much less electroactive than those containing bulky electron-donor t-butyl groups.

  15. Current Developing Studies • The chemistry of electroactivity of phenoxyl species is being developed with several di- and trivalent ions in order to evaluate the geometries preferences of the ligands.

  16. References • Anadi C. Dash, Bhaskar Dash, and Prasanna Kumar Mahapatra, J. Chem. Soc., Dalton Trans. 1983,1503. • Nathan E. Hall and Brian J. Smith, J. Phys. Chem., 1998, 102, 4930-4938. • Margaret Brault, Ralph M. Pollack, and Charles L. Bevins, J. Org. Chem.,Vol. 41, No. 2,1976 • Jack Hine, Francis A. Via, Judith K. Gotkis, and John C. Craig, Jr., Journal of the American Chemical Society,1 92:17 / August 26, 1970

  17. Thanks • Dr. Schlegel • Dr. Hrant P. Hratchian • Marco Mallard • Barbara • Others

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