Structural Conformational Study of Eugenol Derivatives Using Semiempirical Methods

Radia Mahboub

doi:10.1155/2014/490358

Abstract

We investigated the conformational structure of eugenol and eugenyl acetate under torsional angle effect by performing semiempirical calculations using AM1 and PM3 methods. From these calculations, we have evaluated the strain energy of conformational interconversion. To provide a better estimate of stable conformations, we have plotted the strain energy versus dihedral angle. So, we have determined five geometries of eugenol (three energy minima and two transition states) and three geometries of eugenyl acetate (two energy minima and one transition state). From the molecular orbital calculations, we deduce that the optimized trans form by AM1 method is more reactive than under PM3 method. We can conclude that both methods are efficient. The AM1 method allows us to determine the reactivity and PM3 method to verify the stability.

Highlights

Eugenol (4-allyl-2-methoxyphenol) is a phenylpropene, an allyl chain-substituted guaiacol
We investigated the conformational structure of eugenol and eugenyl acetate under torsional angle effect by performing semiempirical calculations using AM1 and PM3 methods
We have evaluated the strain energy of conformational interconversion

Summary

Introduction

Eugenol (4-allyl-2-methoxyphenol) is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a phenol derivative used in many areas such as perfumes, flavorings agent, and dental materials. It is used as an antiseptic, analgesic, fungicide, bactericide, insecticide, anticarcinogenic, antiallergic, antioxidant, antiinflammatory, and so forth [15–17]. We investigated the conformational structure of eugenol and eugenyl acetate under torsional angle effect by performing semiempirical calculations using AM1 and PM3 methods. From these calculations, we have evaluated the strain energy of conformational interconversion to provide a better estimate of stable conformations. These results can be used to make future applications possible (Figure 1)

Methodology

Results and Discussion

Conclusion