STRUCTURAL CHARACTERIZATION OF ORGANIC COMPOUNDS
Academic year and teacher
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- Versione italiana
- Academic year
- 2016/2017
- Teacher
- GIANCARLO FANTIN
- Credits
- 6
- Didactic period
- Secondo Semestre
- SSD
- CHIM/06
Training objectives
- The aim of the course is to provide students with the tools to determine the structure of organic molecules from the combined analysis of the infrared (IR), mass (MS) and nuclear magnetic resonance (NMR) spectra.
The main acquired knowledge will be:
• 13C NMR spectroscopy;
• Vectorial description of the NMR phenomenon;
• Pulse and Fourier Transform NMR (also called pulse-FT NMR);
• Description and analysis of the main NMR one-dimensional pulse sequences;
• Origin of a two-dimensional NMR spectrum (NMR-2D);
• Description and analysis of some NMR-2D sequences.
The basic acquired abilities will be:
• Critically analyze a simple NMR pulse sequence;
• Interpreting the various types of 1D- and 2D-NMR spectra;
• Derive the structure of organic molecules from the combined analysis of infrared spectra (IR), mass spectra (MS) and nuclear magnetic resonance spectra (NMR). Prerequisites
- The students should be able to interpret the 1H NMR spectra of simple organic molecules and, in addition, the knowledge of basic organic chemistry is required.
Course programme
- In the course of 36 hours, will be treated the following topics:
• 13C NMR spectroscopy, (3 – 4 hours):
Sensitivity; chemical shift; homo- and hetero-nuclear coupling constants; signal integration; fully coupled spectra, Broad-Band decoupled spectra and off-resonance decoupled spectra; single frequency on-resonance decoupling technique (SFORD); nuclear Overhauser effect (n.O.e.).
• Vectorial description of the NMR phenomenon, (4 – 5 hours):
continuous wave and Fourier transform spectroscopy (CW and FT spectroscopy); net magnetization vector; rotating frame; radiofrequency pulse or "RF pulse"; pulse length an phase; free induction decay (FID) and receiver phase; evolution of the transverse magnetization due to chemical shift and coupling constants.
• Pulse and Fourier Transform NMR (also called pulse-FT NMR), (4 – 5 hours):
definition of pulse sequence; description and analysis of the main 1D-NMR pulse sequences: Inversion Recovery, SPIN-ECHO, APT e DEPT.
• Origin of a two-dimensional NMR spectrum, (1 hour).
• Description and analysis of some NMR-2D sequences: J-RESOLVED, COSY and INADEQUATE, (2 hours).
• Description and method of interpretation of the main 2D-NMR spectra: J-RESOLVED, COSY, DELAYED COSY, DFQ-COSY, NOESY, HETCOR, HMQC, HMBC, INADEQUATE, TOCSY, ROESY (2 – 3 ore).
• Outline of multidimensional NMR spectroscopy, (1 hour).
• Outline of Magnetic Resonance Imaging, (1 hour).
• In the remaining hours will be conducted exercises on the interpretation of various types of the NMR spectra: in particular C13 and two-dimensional NMR ones. It will also determined a wide range of structure of organic molecules from the combined analysis of IR, MS and NMR spectra. Didactic methods
- Frontal lectures on all the course’s topics. It will also view websites dedicated to nuclear magnetic resonance.
Learning assessment procedures
- The aim of the exam is to verify at which level the learning objectives previously described have been acquired. In particular, students will have to determine the structure of one organic molecule from the combined analysis of its infrared (IR), mass (MS) and nuclear magnetic resonance (NMR) spectra. In addition, each student will be required to prepare a report in which explain the rational path followed to determine the final structure.
The time allowed for this test is 2 or 3 hours. . It is allowed consulting any textbook or correlation tables.
To pass the test you must correctly identify the structure of the compound (18/30): the assessment of the report allows you to raise the vote until 30/30.
To get the praise (30 and lode) will require an additional oral exam to test the ability to reason about different topics covered during the course. Reference texts
- Teacher’s handouts
R. M. Silverstein, F. X, Webster;
Spectrometric identification of organic compounds.
Ed. John Wiley & Sons, Inc.
Italian edition:
Identificazione spettroscopica di composti organici.
Seconda Edizione
Casa Editrice Ambrosiana.
