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The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 30
(2025) pp 50-57
An Expeditious and Flexible Computational Exercise to Teach Heterocycle Acylation
Adam B. Riddell, Adrian L. Schwan⁎
Department of Chemistry, University of Guelph, 50 Stone Rd. E, Guelph, ON, Canada N1G 2W1, schwan@uoguelph.ca
Received November 18, 2024. Accepted February 07, 2025.
Published: 18 March 2025
Abstract. A set of inexpensive, rapid and pedagogically beneficial computational experiments focused on the electrophilic acylation of furan and N-substituted pyrroles have been designed with the intent of inclusion into an upper year organic chemistry/heterocycle course or laboratory. The purpose of these experiments is to give students a larger breadth of information on the chemistry of 5-membered heterocycles, more experience with computational chemistry concepts/procedures, and a hands-on example for applying the Hammond Postulate to a chemical system. The main software tools utilized for this activity are Gaussian/Gaussview and ChemDraw which are accessible with an academic license. Details of our implementation and the educational value of this work are discussed. Suggestions for how the experiment could be evaluated are also provided. Gaussian output files are provided if the search for transition states is not part of a student’s exercise.
Key Words: Computers in Chemistry; physical chemistry; organic chemistry
(*) Corresponding author. (E-mail: schwan@uoguelph.ca )
Article in PDF format(444 KB) HTML format
Supporting Materials:
A Supporting Information file contains i) additional computation details, ii) selected structure images, iii) a set of instructions for performing calculations on structures related to the alpha acetylation of furan, and iv) XYZ coordinates of optimized structures. Log files for optimized structures are also separately available, separately. (1062 KB)
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