1. Knowledge and understanding
At the end of the course, the student must have acquired the basic knowledge on the spectroscopic techniques currently used for identification and for the structural and conformational study of organic compounds.

2. Applying knowledge and understanding
At the end of the course, the student must be able to apply the knowledge acquired for the recognition of the structure of unknown organic substances, interpreting the IR, NMR and mass spectra.

3. Making judgements
at the end of the course the student must be able to work autonomously, coordinating the information obtainable from the spectra, so as to obtain a univocal solution. This knowledge can be used in subsequent courses, in the development of the thesis, in a working environment.

4. Communications skills
at the end of the course the student must be able to clearly present the results and the deductions made with the correct technical language.

5. Learning skills
At the end of the course the student will have the ability to understand the various aspects of the application of these techniques in the chemical and biological field (operating conditions, obtainable information, aspects related to safety, environment and economic) and will be able to deepen in autonomously the topics covered in the course, including through the consultation of texts, specific bibliography.

The student who accesses this course must be familiar with organic chemistry, in particular the major classes of organic compounds and the main types of organic reactions. Must possess the basics of thermodynamics and physics. Prerequisites: Organic Chemistry.

In this course the following topics will be taught: interaction between molecular systems and electromagnetic radiation; UV-visible spectroscopy; infrared spectroscopy; NIR spectroscopy; Raman spectroscopy; nuclear magnetic resonance spectroscopy; mass spectrometry. For each spectroscopy technique we will discuss basic principles, describe the instruments, and practice with exercises for the characterization of molecules.

R.M. Silverstein, F.X. Webster, D.J. Kiemle, D.L. Bryce "Identificazione Spettrometrica di Composti Organici", CEA, Casa Editrice Ambrosiana, Milano, III ed., 2016.

M. Hesse, H. Meier, B. Zeeh. Metodi Spettroscopici nella chimica organica, II Edizione, EdiSES, Napoli, 2010.
Skoog, Holler, Crouch, Chimica Analitica Strumentale, II Edizione, EdiSES, Napoli, 2009.
Cinzia Chiappe, Felicia D'Andrea, Gerardo Abbandonato, Tecniche spettroscopiche e identificazione di composti organici. Problemi svolti e da svolgere. ETS, 2011.

Introduction. Introduction to spectroscopic methods. Interaction between molecular systems and electromagnetic radiation. Characterization of an electromagnetic wave. Fundamental relationships. The electromagnetic spectrum. Energy levels in atoms. Energy levels in molecules. Electronic, vibrational, rotational, nuclear spin transitions. Absorption and emission of energy. Planck's equation. Spectral zones of different types of transitions.
UV-Visible spectroscopy. General principles and instrumentation. Electronic transitions: allowed and forbidden. Chromophores and typical values of absorption Band characteristics: wavelength, width, intensity. Contributions related to the substituent groups. Shift bathochromic, ipsochromic, auxochromic. Solvent effect. Emission spectra. Fluorescence.
Infrared spectroscopy. Principles of the method. Continuous wave instrumentation. FTIR. Sample preparation. Gaseous, liquid, solid samples. Reflection spectroscopy. DRIFTS. ATR.
Normal vibration modes: stretching and bending. Degrees of freedom and vibrations. Type of absorption bands: fundamental bands, overtones, combination bands. Harmonic and anharmonic oscillator model. Hooke's law. Spectral zones. Main vibrational frequencies of the most important functional groups. Alkanes, alkenes, alkynes, aromatics. Alcohols and phenols. Effect of hydrogen bonding. Ethers. Amines. Carbonyl group: aldehydes, ketones, carboxylic acids, esters, amides. Nitriles. Sulfur compounds. Nitroderivatives. Halogen derivatives.
NIR spectroscopy. General principles. Spectral field. Bands. Quantitative measures. Calibration. Instrumentation. Examples of application in quantitative analysis and quality control.
Raman spectroscopy. Principles of the method. Stokes and anti-Stokes lines. Polarization and Raman band. Instrumentation. Application examples.
Nuclear Magnetic Resonance. Principles of the method. Continuous wave instrumentation. Fourier transform. Radiofrequency impulses. FID. Preparation of NMR samples. Deuterated solvents. Reference. Basic parameters of the NMR. Chemical shift: inductive effects, hybridization, anisotropy in systems containing electrons. Protons linked to heteroatoms: effect of hydrogen bond (concentration and temperature), exchange effect; quadrupole effect. Signal integration. Coupling and multiplicity of signals. Chemical and magnetic equivalence. Coupling constant. Effect of B0. Typical values of geminal, vicinal and long range coupling constants in open, cyclic, vinyl and aromatic systems. Spectra of the first order and second order. Eq. of Karplus. Tree diagrams for the interpretation of complex multiplets. Virtual coupling. Homotopic, enantiotopic, diastereotopic nuclei. Symmetrical chains. Shifts reagents for the study of chiral compounds. 13C NMR spectroscopy: typical values of chemical shifts and J(13C-1H). H-1 and C-13. NMR spectra of the main classes of organic compounds.
NMR spectroscopy of other nuclei: F-19, P-31, N-15.
Mass Spectrometry. General principles of mass spectrometry. Ionization and fragmentation. Mechanisms of homolytic and heterolytic fragmentation. Rearrangements and transpositions. Ion and radical stability. The molecular peak at high and low resolution. Isotopic peaks. Molecular ion and molecular formula. Main fragmentations characteristic of functional groups.
Instrumentation
Interpretation of IR,

Lectures using both power point presentation and black board.
Classroom exercises on the interpretation of IR spectra, H1-NMR, C-13-NMR, MS, first for each type, then with the combined use of all techniques.
These exercises are similar to those proposed in the examination.

All the powerpoint presentations are available (Moodle).
Any changes to the methods described here, which become necessary to ensure the application of the safety protocols related to the COVID19 emergency, will be communicated on the websites of the Department and of the course.

The final exam includes a written test.
The written test (3h) consists in the recognition of the structure of an organic compound on the basis of mass spectra, IR, NMR, in a similar way to the exercises carried out in the classroom.
In this test the structure of the compound must be identified and the spectra interpreted in detail, so as to prove to be able to operate independently and decide which is the correct structure based on the information provided.