Enrollment year
2020/2021
Academic discipline
CHIM/06 (ORGANIC CHEMISTRY)
Department
DEPARTMENT OF DRUGS SCIENCES
Course
MEDICINAL CHEMISTRY AND PHARMACEUTICAL TECHNOLOGY
Curriculum
PERCORSO COMUNE
Period
1st semester (04/10/2021 - 28/01/2022)
Lesson hours
80 lesson hours
Activity type
WRITTEN TEST
Prerequisites
To attend this course the basic knowledge provided by the courses of General and Inorganic Chemistry and Organic Chemistry 1 of the first year of course are required
Learning outcomes
At the end of the course the student will have in-depth study the reactivity of some classes of organic compounds have already been introduced in the course of Organic Chemistry 1, and he will have acquired a general knowledge of the nomenclature, preparation and reactivity of the most common heterocyclic compounds. This knowledge is a prerequisite for the study of Medicinal Chemistry. He will also acquire the basic knowledge on the chemistry of natural organic substances, in order to prepare the biochemistry studies. Finally, the student will acquire the fundamental principles of the main types of spectroscopy: UV, IR, NMR and mass spectrometry and will be able to correct use of the spectroscopic data to identify the structure of simple organic compounds.
Course contents
Reactivity (Part A): The first part of the course deals with a review and in-depth analysis of organic stereochemistry: CIP rules, stereocenters, elements of stereogenicity and topicality of faces, atoms and groups. Kinetic and thermodynamic control in the formation of enolate. Elements of asymmetric synthesis, kinetic resolutions and dynamic kinetics. Chemistry of enols and enolates, with particular reference to the stereochemical course, transition states of Zimmerman-Traxler and rules of Cram and Felkin-Ahn. Elements of organocatalysis.
The central part of the course will be dedicated to the study of heterocyclic compounds. After the exam
of the nomenclature, the concept of aromaticity referred to heterocyclic nuclei will be re-discussed and the
essential characteristics that differentiate electron-rich and electron-poor nuclei. The systematic study of the
main methods of preparation and general reactivity of classes of heterocyclic compounds, emphasizing similarities and
differences with the aromatic compounds studied in the organic course 1. Outline of reductions and oxidations in organic chemistry: hydrogenations in the hetero- and homogeneous phase (Wilkinson, Crabrtee). Asymmetric Noyori reductions. Most common oxidants, PCC, Dess-Martin, TPAP, and Swern.
Spectroscopy (Part B): After a brief introduction on the fundamental principles of spectroscopy, we will see their
application in UV-visible spectroscopy, taking into consideration the instrumentation, the recording and interpretation of a spectrum, and the potential applications in quantitative and qualitative analysis. In the next section, devoted to the study of IR-spectroscopy, along with the study of the various types of vibrational excitations, we will briefly discuss the instrumentation and the problems correlated to the sample preparation. Moreover, we will proceed to a detailed analysis of the different spectral regions. More emphasis will be given to the study of proton Nuclear Magnetic Resonance spectroscopy (1H-NMR): we will discuss the principles of this technique, followed by a detailed analysis of the physical parameters (chemical shift, coupling constant, etc.) that can be used to gain structural information. In the last part of the course we will examine dynamic effects in NMR spectra and briefly introduce other topics such as two-dimensional NMR spectroscopy (2D-NMR), Correlation Spectroscopy (COSY), Nuclear Overhauser Effect (NOE), 13C-NMR spectroscopy, and DEPT techniques. In the mass spectrometry section we will study the principal components of a mass spectrometer, the main ionization techniques, the “nitrogen rule”, and the isotopic patterns resulting from the presence of halogen atoms.
Teaching methods
Lectures carried out by means of presentations (PowerPoint) projected onto the screen and insights on the blackboard. Exercises will also be proposed and solved by the teacher in preparation for the written test.
Reccomended or required readings
Loudon, Chimica Organica, EdiSeS;
Brown, Chimica Organica, EdiSES;
Davies, Aromatic Heterocyclic Chemistry, Oxford University Press;
Ege, Chimica Organica, Editrice Ambrosiana;
Broggini, Zecchi, Chimica dei Composti Eterociclici, Zanichelli;
Sica, Zollo, Chimica dei Composti Eterociclici, EdiSES;
Harwood, Claridge, Introduction to Organic Spectroscopy, Oxford Science Publications;
Silverstein, Webster, Identificazione Spettrometrica di Composti Organici (terza edizione), CEA;
Chiappe, D’Andrea, Tecniche spettroscopiche e identificazione di composti organici, Edizioni ETS.
Assessment methods
An on-going test, that will take place before the Christmas break, will be conducted on the reactivity part (Part A).
The final written exam is divided into two parts: reactivity (Part A) and spectroscopic methods (Part B). The overall vote will be derived from the arithmetic mean of the obtained votes. Regarding the Part A, the vote will result in 2/3 of open-ended questions or exercises concerning the theoretical part, and 1/3 of short synthetic sequences that the students will have to solve to demonstrate that they have correctly assimilated the lectured concepts. Regarding Part B, the vote will come to 50% by theoretical questions and 50% by the determination of the structure of an unknown compound using its spectroscopic data.
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