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Mesomerism, Ring & Substituent Effects, A Computational Chemistry Experiments

Djameleddine Khatmi 1, 2 Yannick Carissan 2 Denis Hagebaum-Reignier 2 Nicolas Goudard 2 Stéphane Humbel 2, * 
* Corresponding author
2 CTOM - Chimie Theorique et Modèles
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : The introduction of computational chemistry experiments for undergraduate students in sciences can really facilitate knowledge acquisition. It can make consistent various concepts in chemistry without a lengthy experimental protocol involving synthesis and physical chemistry mesurements. In the present case the students use a very simple molecular modeling program that we implemented: HuLiS. The computational chemistry experiment described herein is devoted to an important concept in chemistry: resonance between Lewis structures (mesomerism). In this context, conjugated ring species, as herein, are somewhat specific in the sense that aromaticity can play an important role. Hence, we discuss here a rather advanced resonance effect, where the usual qualitative rules do not suffice by themselves, but aromaticity and the ―4n+2 electron‖ rule must be considered. This Hückel rule can be numerically displayed with an appropriate computational experiment. We use our free java applet (HuLiS) designed to evaluate the weights of resonance structures. As it is based on Hückel theory, the computations are fast, and the theoretical background is much simpler than with ab initio programs, hence the teachers are likely to master the tool used by the students. Upon substitutions, the weights of the zwitterionic Lewis structures adapt to the electronegativity. This is an opportunity to discuss the role of electronegativity in mesomerism, and strengthen the knowledge of the students.
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Submitted on : Tuesday, October 25, 2016 - 5:31:08 PM
Last modification on : Sunday, January 9, 2022 - 6:06:04 PM
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Djameleddine Khatmi, Yannick Carissan, Denis Hagebaum-Reignier, Nicolas Goudard, Stéphane Humbel. Mesomerism, Ring & Substituent Effects, A Computational Chemistry Experiments. journal of laboratory chemical education, 2016, 4 (2), pp.25-34. ⟨10.5923/j.jlce.20160402.01⟩. ⟨hal-01347226⟩



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