Ateneo - UPO

Infrared spectroscopy (IR) Nuclear magnetic resonance spectroscopy (NMR) Mass spectrometry (MS)

R.M. Silverstein, F.X. Webster, Identificazione spettroscopica di composti organici, Casa Editrice Ambrosiana Additional textbook M. Hesse, H. Meier, B. Zeeh, Metodi spetroscopici in chimica organica, Edises H. Günther, NMR spectroscopy, Wiley Ed.

Provide students with the knowledge of the physical principles underlying the different spectroscopic techniques and instrumentation used for the acquisition of spectra. The course is largely devoted to the interpretation of the spectra obtained with different techniques in order to allow the student to master the different spectroscopies especially from the practical point of view, allowing the student to identify unknown organic compounds.

Knowledge of the structures of the main classes of organic compounds

Lectures with multimedia support and several exercises of structure elucidation.

It will be possible, and highly recommended, to participate to the proposed self-evaluation in-course tests. Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/services-students-physical-or-learning-disabilities. Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects.

Oral test based on the identification of an unknown compound by analysis of IR, NMR and mass spectra, with questions on the theory of the different spectroscopic techniques.

Introduction to spectroscopic methods. Properties of electromagnetic radiation. Electromagnetic spectrum. Absorption and emission spectroscopy. Infrared spectroscopy (IR) – Traditional and Fourier transformation (FT-IR) spectrometers. The harmonic oscillator. Non-harmonicity and quantization. Type of vibrations. Instrumentation and sample preparation. The IR spectrum and characteristic absorptions of functional groups. Fingerprints region. Nuclear magnetic resonance spectroscopy (NMR) – The nuclear spin. Theory of NMR spectroscopy, pulse tecnique and Fourier transformation. Relaxation. Spectral paraneters: chemical shift, spin-spin coupling, integration. 1H NMR: first order spectra. Analysis of main spin systems. Relationship between structure and chemical shift. Symmetry, chirality, dynamic phenomena and NMR spectrum. Spin decoupling and Nuclear Overhauser effect (nOe). 13C NMR: features of 13C nucleus. Decoupled, off-resonance, DEPT e APT spectra. Relationship between structure and chemical shift. Introduction to main 2D omo- and etheronuclear techniques. Mass spectrometry – Instrumentation, hints. Chemical and isotopic mass. Mass and electronic parity. Molecular mass and molecular formula determination. Exact mass and resolution. Choice of ionization method for different class of compounds. Fragmentation and rearrangement reactions of the main classes of organic compounds. Spectra analysis and identification of organic compounds from mass spectra. Illustration of the structural determination of a natural substance.

KNOWLEDGE AND UNDERSTANDING- The student will be expected to show mastery of the basic knowledge of modern spectroscopic investigation methods as well as the ability to understand the fundamental characteristics of the spectra provided by each substance (NMR, IR and Mass). These skills will be assessed through both written and oral evidence. APPLYING KNOWLEDGE AND UNDERSTANDING- The student will be expected to show possession of the ability to apply her/his knowledge, and the ability to identify the presence of molecular fragments of varying complexity in a way that defines how these fragments are related to each other, through the combined analysis of spectra obtained with the various techniques as well as that of simulation of spectra given a certain substance. These skills will be assessed through both written and oral tests. MAKING JUDGMENS - The student should be able to focus attention on a given structural problem, and decide which methods are most useful in solving it. These skills will be assessed during the oral interview through application-oriented oral questions. COMMUNICATION- The student should be able to communicate clearly and in appropriate language her/his knowledge and interpretative skills of the various spectra to specialists and nonspecialists. These skills will be assessed through the oral test. LEARNING SKILLS- The student(s), by the end of the course, should have developed a good autonomy in identifying the structures of unknown organic molecules. This ability, to the extent possible, will be stimulated by the lecturer by proposing insights and providing exercises to be solved during the course and discussed during lectures.