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Chemistry 473: Structure Determination and Reaction Analysis

Course Level: 
Fourth Year
Academic Year: 
2018/2019

Prerequisite: CHEM 245 and one of CHEM 313, CHEM 318, CHEM 330

Overview

This course will present an advanced treatment of the structural determination and reaction analysis of small molecules using modern spectroscopic and spectrometric techniques. A particular emphasis will be placed on the integration of UV-visible (UV-vis) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry (MS) data with nuclear magnetic resonance (NMR) spectroscopy to solve structural problems.  NMR topics will primarily include H-1 and C-13 analyses, but will also extend to other nuclei, variable temperature NMR, and multidimensional experiments.  Students will come away with a skill set to solve sophisticated structure determination problems in organic and organometallic/inorganic chemistry.

This course is designed for advanced Chemistry majors and Honours students who seek future employment in the chemical, pharmaceutical, and biotechnical industries, as well as academia. Students in other programs (e.g. Biochemistry, Pharmaceutical Sciences, Forestry) having the appropriate prerequisite courses will find the content extremely beneficial as they transition to related careers. 

This course is strongly recommended for students interested in future graduate study in organic or organometallic chemistry.  For advanced students seeking to develop further knowledge in the application of multidimensional NMR analysis for de novo organic structure solution, the content of CHEM473 is specifically designed to link with the graduate-level course CHEM573, Application of Spectroscopy to Organic Structural Determinations, held in the following term.

Literature

Textbook:  Introduction to Spectroscopy, 5th ed., by Pavia, Lampman, Kriz, and Vyvyan (Cengage Learning, ISBN 978-1285460123)

Workbook: Organic Structures from Spectra, 5th ed., By Field, Sternhell, and Kalman (Wiley, ISBN 978-1118325490)

Additional examples and reading material may be drawn from the primary research literature.

Grading

Final course grades will be determined from in-class/take-home assignments (10%), one mid-term examination (35%), and one final examination (55%).

Course contents

Molecular formulas (ca. 1.5 lecture hours)

Elemental analysis, degree of unsaturation, rule of 13

Ultraviolet/visible spectroscopy (ca. 3.0 lecture hours)

UV/vis principles and instrumentation

UV/vis spectra and problems

Infrared spectroscopy (ca. 4.5 lecture hours)

IR principles and instrumentation

IR spectra and problems

Small-molecule mass spectrometry (ca. 7.5 lecture hours)

MS principles and instrumentation (especially EI, CI, ESI, MALDI; low- and high-resolution MS)

MS fragmentation: principles, chemistry, pathways

MS spectra and problems

Nuclear magnetic resonance spectroscopy (ca. 15 lecture hours)

Principles and instrumentation

Chemical shifts (shielding/anisotropy) and integration

Simple H-H spin coupling

Advanced spin-spin coupling

Exchange, temperature, the NMR timescale, decoupling

C-13 NMR, heteronuclear coupling/decoupling

NMR of other nuclei

2-D NMR (especially COSY, HETCOR, NOESY)

Integrated problems (ca. 4.5 lecture hours)

Solution of structural problems using multiple confirmatory datasets