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CHEM 430 – Structural Analysis of Organic Compounds

Spring 2014. CHEM 430 – Structural Analysis of Organic Compounds. Introduction. Our approach must differ depending on the type of work we are performing. “ Cold ” analysis – the unknown organic is a complete unknown Forensic chemistry EPA methods and related analyses

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CHEM 430 – Structural Analysis of Organic Compounds

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  1. Spring 2014 CHEM 430 – Structural Analysis of Organic Compounds

  2. Introduction Our approach must differ depending on the type of work we are performing. • “Cold” analysis – the unknown organic is a complete unknown • Forensic chemistry • EPA methods and related analyses • Natural products taxonomy In these cases, little if anything is known about the individual compounds – detective work must recreate the entire structure • Results of a synthetic experiment In this case, the majority of the structure should be maintained, the goal is to analyze for and confirm changes • Characterization for the chemical literature – Assignments! The analysis here is to confirm the author’s findings and serve as a benchmark for further work on the compound

  3. Introduction All approaches will involve a general flow of information:

  4. Methods in General Use

  5. NMR Spectroscopy

  6. NMR Spectroscopy

  7. NMR Spectroscopy

  8. NMR Spectroscopy

  9. Mass Spectrometry

  10. Vibrational Spectroscopy

  11. Electronic Absorption Spectroscopy

  12. Limitations (and grades) We can only see what our ‘shutter speed’ allows:

  13. Limitations (and grades) Harrisonin Can we ever achieve a fully secure structure (or why did I get it wrong?)? Heterocycles1976, 5, 485. J. Nat. Prod. 1997, 60, 822

  14. Limitations (and grades) Can we ever achieve a fully secure structure (or why did I get it wrong?)? J. Am. Chem. Soc. 1983, 105, 6312. Tetrahedron Lett. 1992, 33, 3711 J. Antibiotics 1986, 39, 1527

  15. Limitations (and grades) Can we ever achieve a fully secure structure (or why did I get it wrong?)? J. Org. Chem. 2001, 66, 8717. Tetrahedron Lett. 2003, 44, 1203

  16. Limitations (and grades) Can we ever achieve a fully secure structure (or why did I get it wrong?)? J. Nat. Prod. 2000, 63, 1677. J. Nat. Prod. 2003, 66, 716

  17. Limitations (and grades) Can we ever achieve a fully secure structure (or why did I get it wrong?)? Spirastrellolide J. Am. Chem. Soc. 2003, 125, 5296. Org. Lett. 2004, 6, 2607

  18. Limitations (and grades) (+)-Neopeltolide Can we ever achieve a fully secure structure (or why did I get it wrong?)? J. Nat. Prod. 2007, 70, 412. J. Am. Chem. Soc. 2008, 130, 804

  19. Welcome to CHEM 430 • Assumptions: • Working knowledge of general and organic chemistry • You have seen basic IR and NMR before • Math skills permit solution of algebra and trigonometric problems and a rudimentary understanding of simple calculus

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