Spectroscopic Methods in Organic Chemistry

GENERAL: electromagnetic spectrum and electromagnetic radiation, electromagnetic radiation characterization, electromagnetic radiation and interactions with matter, spectroscopic techniques.
INFRARED SPECTROSCOPY: fundamental principles, frequency of infrared absorption, and chemical structure. Systematic part: hydrocarbons (alcohols, alkenes, alkynes, aromatics), alcohols, ethers, halides, carbonyl compounds, and amines. Combined examples. Instrumentation and recording, IR Spectrophotometer and Fourier Transform IR (FT-IR). Evolution and applications of IR spectroscopy.
NUCLEAR MAGNETIC RESONANCE, NMR: general principles, nuclear properties, magnetic field, and electromagnetic radiation (radiofrequency).
Proton nuclear resonance: 1H NMR observation in a stationary and rotating reference system, resonance spectrum of an isolated proton and real protons in different intensity magnetic fields, spectral amplitude, chemical displacement intervals, internal reference, chemical displacement in hertz and ppm.
Examples of non-coupled systems and assessment of the structure's influence on chemical displacement.
Coupled systems: the spectrum of ethyl acetate, multiplicity of signals, general principles.
Coupling with equivalent protons, non-equivalents, and mixed systems, describing the multiplicity of signal through the cascade diagrams.
Examples of simple coupled systems: assessment of the structure's influence on chemical displacement and the multiplicity of signals.
Coupling constants and structure: geminal, vicinal, and long-range couplings.
Exercise on a collection of proton spectra of simple non-aromatic compounds.
Chemical shift and structure, chemical shift equivalence: random, isochronal protons, homotopic protons, enantiotopic, diastereotopic. Magnetic Equivalence.
Examples: keto-enol equilibria, limited rotation, alicyclic compounds
Practice on a collection of proton spectra of simple aromatic compounds, spin system simulation (cascade diagrams), and reading of spin systems (determination of coupling constants and chemical shift).
Protons on heteroatoms: Oxygen, Nitrogen, and Sulfur.
Experiments of double resonance with examples.
NOe differential experiments with examples.
Nuclear magnetic resonance of carbon-13: general principles, relative and absolute sensitivity of an NMR experiment, chemical shifts, proton-proton and proton-carbon coupling, examples of simple aromatic and non-aromatic compounds, 13C-NMR spectra recorded with the APT and DEPT techniques.
Instrumentation: subtraction of reference frequency, analog-to-digital converter (ADC), ADC characteristics (Acquisition time (At), sampling rate, digital resolution (Rd)), radio frequency pulse (PW, pulse width), impulse duration, and spectral amplitude.
Acquisition sequences: 1H-NMR, 1H-NMR with selective decoupling, 1H-NMR nOe-diff, 13C NMR with 1H / 13C coupling, 13C-NMR decoupled 1H / 13C, 13C NMR APT, 13C NMR DEPT.
Nuclear magnetic resonance of other nuclei: general principles, nuclear magnetic resonance of the 15N. Reading spectra coupled and decoupled from the proton. 19F and 31P nuclear magnetic resonance imaging. Reading spectra coupled and decoupled from proton, reading proton spectra, and carbon-containing fluorine and phosphorus compounds.
Two-dimensional magnetic resonance spectroscopy (2D). COrrelation Spectroscopy COSY, HSQC; HMBC, NOESY, and TOCSY.
Examples combined with 2D techniques.
MASS SPECTROMETRY: General principles and instrumentation. Sources (EI, CI, FAB, MALDI, ESI APCI), analyzers (magnetic, quadrupole, ion trap), detectors. Analysis of a mass spectrum: molecular ion, fragment ions, general classification of fragmentation reactions. Systematic part: fragmentation reactions of the main classes of organic compounds with exercises.
Final Exercises on Structural Determination of Organic Compounds with Combined Techniques.