CARATTERIZZAZIONE STRUTTURALE DI MOLECOLE ORGANICHE

Students will acquire qualifications and develop the methodologies for the interpretation of mass (MS), infrared (IR), ultraviolet-visible (UV-Vis) and nuclear magnetic resonance spectra (both 1D and 2D NMR). At the end of the course students will be able to carry out a complete structural elucidation of organic molecules, by applying the whole spectroscopic techniques studied.

The course will be structured with both frontal lessons and classworks.

The course will consist of:

Intoduction on spectroscopic techniques.

Mass spectrometry: Introduction and Mass spectra analysis of the most common classes of organic compounds. Classworks.

Infrared spectroscopy: Introduction on the nature of IR spectroscopy. Absorption range and most common IR bands of organic moleucles. Classworks.

UV-Vis absorption spectroscopy: Introduction to UV-Vis spectroscopy and classificiation of UV absorption bands. Important UV chromophores. Classworks.

General Introduction to Nuclear Magnetic Resonance Spectroscopy: The physics of nuclear spins and instruments.

¹H NMR: Chemical shift in ¹H NMR. Spin-spin coupling. Analysis of ¹H NMR. Classworks.

¹³C NMR: Shielding and characteristic chemical shifts in carbon spectra. Coupling and Decoupling in ¹³C NMR spectra. Classworks

¹H NMR spectra in determining the structure of organic molecules: The effect of chirality. The Nuclear Overhauser Effect (NOE). Solvent-induced shifts. Classworks.

Dynamic processes in NMR: The NMR time-scale.

The 2D NMR: Homonuclear correlation spectroscopy. Analysis of ¹H-¹H COSY, ¹H-¹H-TOCSY, ¹H-¹H NOESY and ROESY. Heteronuclear correlation spectroscopy. Analysis of ¹H-¹³C COSY (HETCOR) and longrange ¹H-¹³C (HMBC) spectra. Classworks.

The NMR spectra of other-nuclei: ¹⁵N NMR, ¹⁹F NMR, ³¹P NMR spectra analysis.

Practice excercises.

1) R.M. Silverstein, F.X. Webster e D.J. Kiemle, IDENTIFICAZIONE SPETTROSCOPICA DI COMPOSTI ORGANICI, Casa Editrice Ambrosiana (Milano)

2) L.D. Field, S. Sternhell, J.R. Kalman, ORGANIC STRUCTURES FROM SPECTRA, IV Edizione, John Wiley and Sons (Chichester New York Brisbane Toronto Singapore)

3) M. Hesse, H. Meier, B. Zeeh, METODI SPETTROSCOPICI IN CHIMICA ORGANICA, EdiSES (Napoli).

4) Digital learning material available at www.studium.unict.it