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Course unit
PHYSICAL METHODS IN BIOORGANIC CHEMISTRY
SCP3056653, A.A. 2019/20
Information concerning the students who enrolled in A.Y. 2017/18
ECTS: details
Type |
Scientific-Disciplinary Sector |
Credits allocated |
Educational activities in elective or integrative disciplines |
CHIM/06 |
Organic Chemistry |
6.0 |
Course unit organization
Period |
First semester |
Year |
3rd Year |
Teaching method |
frontal |
Type of hours |
Credits |
Teaching hours |
Hours of Individual study |
Shifts |
Laboratory |
1.0 |
16 |
9.0 |
No turn |
Lecture |
5.0 |
40 |
85.0 |
No turn |
Examination board
Board |
From |
To |
Members of the board |
6 METODI FISICI IN CHIMICA BIORGANICA 2018-2019 |
01/10/2018 |
30/11/2019 |
SAIELLI
GIACOMO
(Presidente)
GOBBO
MARINA
(Membro Effettivo)
ZOLEO
ALFONSO
(Supplente)
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Prerequisites:
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Knowledge and understanding of general organic chemistry and physical chemistry. |
Target skills and knowledge:
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The course will provide students with the means to interpret spectra obtained with the most common techniques used for structural elucidation of molecules: mass spectrometry (MS), applied to small organic molecules and proteins; infrared (IR) spectroscopy, for organic molecules and proteins; nuclear magnetic resonance (NMR), applied to small organic molecules and natural substances. |
Examination methods:
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Written test: multiple choice tests and interpretation of spectra of unknown compounds |
Assessment criteria:
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The student must demonstrate the ability to interpret MS, IR and NMR spectra and to be able to guess the correct molecular structure from the analysis of the spectra. |
Course unit contents:
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Lectures:
Principles of organic chemistry: functional groups, nomenclature, inductive and resonance effects.
General principles about the spectroscopic techniques of structural elucidation.
Mass Spectrometry (MS): Ionization methods: electron impact, chemical ionization, MALDI, ESI. Ion separation methods: magnetic, quadrupolar and time-of-flight analyzers. Molecular ion, isotopic ions, metastable ions. Mass spectrometry to study proteins: peptide fingerprinting, peptide sequence tag.
Infrared spectroscopy (IR): IR resonances of the principal functional groups of organic chemistry and proteins.
Nuclear Magnetic resonance (NMR): chemical shift and shielding constant. Factors influencing the chemical shift: electronic structure and π electrons. Additivity rules. Coupling constant J. Spin multiplicity and its origin. Geminal, vicinal and long-range coupling. Factors influencing the coupling constant. Chemical shift and coupling in hydrogen atoms bonded to O, N and S atoms.
Chemical and magnetic equivalence, enantiotopic and diastereotopic protons. First order and higher order spectra. Dynamic NMR. Couplings with heteroatoms (C-13, F-19, P-31). Decoupling and NOE effect.
Exercise:
Problem of interpretation of MS, IR and NMR spectra of unknown compounds
Laboratory:
Preparation of samples of unknown compounds for MS, IR and NMR spectra. Acquisition and analysis of the spectra. Extraction of natural substances and subsequent identification. |
Planned learning activities and teaching methods:
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Lectures, exercise, laboratory experiments |
Additional notes about suggested reading:
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Lecture notes, downloadable from the lecturer web site, suggested text |
Textbooks (and optional supplementary readings) |
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Silverstein, Robert M.; Webster, Francis X.; Pinna, Luigi; Rassu, Gloria; Casiraghi, Giovanni; Zanardi, Franca, Identificazione spettroscopica di composti organiciRobert M. Silverstein, Francis X. Websteredizione italiana a cura di Giovanni Casiraghi, Luigi Pinnahanno collaborato alla traduzione Gloria Rassu, Franca Zanardi. Milano: CEA, 1999.
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