Theoretical Study of 1,3-Dipolar Reactions of Myrcene and Trimethylsilylazide

Title:Theoretical Study of 1,3-Dipolar Reactions of Myrcene and Trimethylsilylazide

Volume: 14 Issue: 3

Author(s): Sepehr Taban*Avat Arman Taherpour*

Affiliation:

• Department of Organic Chemistry, Faculty of Chemistry, Razi University, P.O. Box: 67149-67346, Kermanshah,Iran

• Department of Organic Chemistry, Faculty of Chemistry, Razi University, P.O. Box: 67149-67346, Kermanshah,Iran

Keywords: Myrcene, trimethylsilylazide (TMS-N3), [3+2] cycloaddition reaction, 1, 2, 3-triazoline, DFT-B3LYP method, molecular modeling.

Abstract: Background: Triazoline derivatives are important group of the heterocycle compounds possessing interesting medicinal and biological properties. Triazoline compounds can be applied in medicine because of their pharmaceutical properties as antiviral, antibacterial, anti-cancerous, antiasthmatic, analgesic and anti-inflammatory medicines. The essential oil of many plants contains Myrcene. The 1,3-cycloaddition reaction pathways of Myrcene with trimethylsilylazide were investigated to obtain the theoretical possibilities of the interesting varieties of its 1,2,3-triazoline derivatives.

Methods: In this study, the 1,3-dipolar reactions of Myrcene (1) with trimethylsilylazide (TMS-N3; 2), the comparison of the three C=C of 1 in the kinetic and thermodynamic aspects, the structural studies of the 1,2,3-triazoline products and the transition states were investigated. The modeling of the reaction was performed by DFT-B3LYP/6-31G* method. This method was applied on the main configurations with less steric restraint effects. The experimental results of FT-IR were just carried out in this study to pursue the course of the reaction pathways.

Results: The HOMO and LUMO orbital levels, ΔΕHOMO-LUMO gaps, dipole moments, the appropriate atoms Mulliken charges, thermodynamic and kinetic stabilities in vacuum were investigated for the components, transition states and the products (P1-P6) by the DFT method. The four important aspects about determination of the combining a dipolarophile (1) with a 1,3-dipole agents (TMS-N3(2)) to produce P1-P3 were determined.

Conclusion: The kinetic and thermodynamic products of the 1,3-dipolar reactions were determined. The final result is that P4 is the kinetic and P6 is the thermodynamic product of the 1,3-dipolar cycloaddition reaction between Myrcene (1) and TMS-N3(2) during the two explained steps. The experimental results confirm the theoretical achievements.

Cite this article as:

Taban Sepehr*, Taherpour Arman Avat*, Theoretical Study of 1,3-Dipolar Reactions of Myrcene and Trimethylsilylazide, Letters in Organic Chemistry 2017; 14 (3) . https://dx.doi.org/10.2174/1570178613666160609122327

DOI https://dx.doi.org/10.2174/1570178613666160609122327	Print ISSN 1570-1786
Publisher Name Bentham Science Publisher	Online ISSN 1875-6255