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.
Riddell et al. (2025) studied this question.