Chemistry
Name: Spectral Interpretation of Organic Compounds
Catalog Number: 412020Y Hours/Credits: 40/2
Prerequisite(s):
Organic Synthesis, Organic Structural Analysis
Course Description:
This course is a basic course for the graduates in Organic Chemistry major, be a higher level courses after "Organic Structure Analysis". Based on the conclusion form IR, UV - visible spectroscopy, nuclear magnetic resonance (1H, 13C) and the basic principle of organic mass spectrometry, more focused on the relationship of the various spectral parameters, spectra and structure of organic molecules, to clarify the general procedure of spectral interpretation in examples, and introduce the progress of a variety of spectroscopic methods, and chemical means or biogenesis in the spectral analysis to identify the organic molecular structures. Through lectures, self-study and discussion on class, training the skills in spectral analysis, learning scientific way of thinking, this will gradually improve the students’ ability to select appropriate spectral information, to identify the molecular structures of complicated organic compounds and the natural products, the students will get the necessary preparations for the professional laboratory research
Course Content:
Chapter 1 1H-NMR Nuclear spin and nuclear magnetic resonance, relaxation, chemical shift, factors to affect the chemical shifts, chemical shifts and its empirical calculation parameters for all different 1H nuclears, spin coupling and coupling constants, relationships between coupling constants and molecular structures, long-range spin coupling, different nuclear coupling; 1HNMR spectra analysis, nuclear equivalence, general spin systems: AX, AB, AX2, AB2,, the AMX, ABX, ABC, A2X2, A2B2, AA'BB ', ABCD; virtual long-range coupling, deceptively simple spectra, the symmetry of the molecule, methods to simplify spectra, spin decoupling, the NOE and NOE difference spectrum, general procedure for spectra interpretation , spectra simulation. Chapter 2 13C-NMR and 2D NMR spectra 13C-chemical shifts, paramagnetic shielding constant(σ), factors related to 13C-chemical shifts, chemical shifts for various types carbon nucleus and its empirical calculation parameters, spin coupling and coupling constants, 13C-1H, 13C-13C, 13C-2H 13C-Miscellaneous, spin-lattice relaxation (T1), mechanism of T1, measurement of T1 and provided structural information, T1 clarify the molecular structure, 13CNMR mapping technology: coupling spectra, broadband decoupling, Off Resonance Decoupling, Gate Decoupling, Inversion Gated Decoupling, Selective Decoupling, NMR Progress,spin-echo J-modulation and polarization transfer enhanced technology: APT, INEPT, DEPT. two-dimensional nuclear magnetic resonance (2D-NMR) , 2D J-decomposition of the spectra, chemical shift correlation spectroscopy: COSY, CH-COSY, HMQC, COLOC and HMBC and TOSY, NOESY, 2D 13C-13C chemical shift correlation (2D-INADEQUATE). multidimensional NMR: 3D-NMR, 4D-NMR. 13CNMR spectra interpretation and the general procedure; 2D-NMR applications and interpretation model. Chapter 3 IR and UV - visible spectra The characteristics of the infrared spectra, Fourier transform infrared spectra and differential spectra, Near-infrared and far infrared spectra, vibration equation and the frequency of groups, factors related bands location, the general procedure for the Interpretation infrared spectra. UV - visible spectral characteristics, electronic transition types and selection rules, solvent effect, dual-wavelength spectra, derivative spectra, photoacoustic spectra; UV spectra of the conjugated system, K bands and its empirical calculation parameters, factors for stereo-structures, UV spectral analysis, the application of the model compounds, the combination of reagents and the chemical reaction. Chapter 4 Organic Mass Spectra History of organic mass spectrometry, Ion in mass spectrometry, determination of molecular weight and molecular formula, the general fragmentation rules of mass spectrometry, the molecular structure factor for breaking, cleavage types: simple fragmentation(σ-,α-,i-), hydrogen rearrangement break, ring fragmentation; skeleton rearrangements (rd, re, rc); general procedures for the mass spectrometry Interpretation. Chapter 5 Combined spectra for complex molecular The general procedure of the interpretation on the combined spectra, spectral data selection of different molecules, the combined effects of chemical method and other classic analytical data and spectral analysis, biogenic theory and its role in guiding the structural identification of natural product molecules, instance of the combination of spectra for complex molecules.
TextBooks:
1) Edited by Nai-Xing WANG, Nuclear magnetic resonance spectroscopy - Application in Organic Chemistry, Beijing: Chemical Industry Press, 2006. 2) Edited by Yao-Xing ZHAO, Xiang-Yu SUN, Spectral analysis and organic structure identification, China Science and Technology Press, Hefei, 1992. 3) Edited by Robert .M. Silverstein, Francis X.Webster, David J.Kiemle, Spectrometric Identification of Organic Compounds,(Seventh edition), translated by WuXi AppTec (second edition), East China University of Science and Technology Press, 2007.
Reference:
1). R. M.Silverstein, F. X. Webseer, Spectrometric Identification of Organic Compounds (Sixth Editor), New York: John Wiley & Sons, Inc., 1998. 2). Braine Smith, Infrared Spectra Interpretation, CRC, LLC, 1999. 3). E. Breitmaier; W. Voelter, Carbon-13 NMR Spectroscopy, VCH, 3Ed., New York, 1987. 4). Roger. S. Macomber, A Complete Introduction to Modern NMR Spectroscopy, John Wiley & Sons, INC., New York, 1998.