Structure and chemical reactivity of glutaconaldehyde acetate ester: Theoretical study

 

Structure et réactivité chimique de l’ester d’acétate de glutacondialdéhyde : Etude théorique

 

A. Mostefai1*, A. Rahmouni1, Z. Bengharez2, S. Taleb3

1 Laboratoire de Modélisation et de Méthodes de Calculs- Centre Universitaire de Saida,

B.P. 138, Cité En- Nasr-20002- Saida – Algérie

2 Laboratoire de Chimie Organique Physique et Macromoléculaire. Faculté des Sciences. Université D. Liabès ,

Site I, faubourg Ben M’Hidi, W22000-Sidi Bel- Abbès, Algérie

3 Laboratoire de Matériaux & Catalyse- Faculté des Sciences- Université Djillali LIABES, Site I, faubourg Ben M’Hidi,

 W22000-Sidi Bel- Abbès, Algérie

* Corresponding author. E-mail:

Received: 13 March 2009; revised version accepted: 31 May 2009

 


Abstract

   The acylation of the glutaconaldehyde anion (1) with acetic anhydres give rise to known molecule (2) under the name of glutaconaldehyde acetate ester. This compound is a reactional intermediate very much used in many syntheses. Its crystalline structure has been determined by Becher and his collaborators, using X-ray data. The compound has the all-trans configuration. With an aim to obtain more detailed information on the structure, the geometries of this compound were optimized. A good agreement was obtained between our results and the experimental ones. In order to identify the reactional sites and to predict site selectivity of this ester towards electrophilic and nucleophilic attack, various global reactivity and selectivity descriptors such as chemical hardness, chemical potential, softness, electrophilicity were used. Fukui functions (FF), local softness and local philicity were applied to probe the local reactivity and site selectivity. However, the results obtained are not able to make a clear decision on site selectivity. Under this situation, the dual descriptors ?fk, ?sk and multiphilic descriptor ??k, give an aiding hand. Indeed, these descriptors are capable of distinctly identifying the stronger electrophilic and nucleophilic sites within glutaconaldehyde acetate ester. 

 

Keywords: Geometry optimization; reactivity; glutaconaldehyde; ab inito; DFT; Fukui indices; local reactivity descriptors.

 


 

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