Theoretical Insight for the Diels-Alder Reaction Mechanism Between Pyrrole and Acrylonitrile

Abstract

Diels Alder reactions are the best method used for the synthesis of various important molecules. In this study, the reaction mechanism between pyrrole and acrylonitrile, which can be an example of these reactions, is explained by DFT. Using the B3LYP method with the 6-31+G(d,p) basis set, chemical hardness, softness, electrophilicity index, electrochemical potential and thermodynamic properties were calculated. When we calculated these properties with solvents such as toluene, the gap between the HOMO and LUMO orbitals of the product formed as a result of the DA reaction was 9.53 eV in the gas phase, while it decreased to 6.49 eV in the toluene solvent environment. In addition, as a result of the calculations; thermodynamic parameters such as enthalpy, entropy and internal energy increased with increasing temperature, but the Gibbs free energy decreased.

Keywords

• Reaction mechanism
• Transition state
• Diels-Alder
• Thermal properties

Pirol ve Akrilonitril Arasındaki Diels-Alder Reaksiyon Mekanizmasının Teorik Olarak İncelenmesi

Abstract

Diels Alder reaksiyonları çeşitli önemli moleküllerin sentezinde kullanılan en iyi yöntemdir. Bu çalışmada bu reaksiyonlara örnek olabilecek pirol ve akrilonitril arasındaki reaksiyon mekanizması DFT ile açıklanmıştır. 6-31+G(d,p) baz setli B3LYP yöntemi kullanılarak kimyasal sertlik, yumuşaklık, elektrofiliklik indeksi, elektrokimyasal potansiyel ve termodinamik özellikler hesaplanmıştır. Bu özellikleri toluen gibi çözücülerle hesapladığımızda DA reaksiyonu sonucu oluşan ürünün HOMO ve LUMO orbitalleri arasındaki boşluk gaz fazında 9,53 eV iken, toluen çözücü ortamında 6,49 eV'ye düşmüştür. Ayrıca hesaplamalar sonucunda; entalpi, entropi ve iç enerji gibi termodinamik parametreler artan sıcaklıkla artmış, ancak Gibbs serbest enerjisi azalmıştır.

Keywords

• Reaksiyon mekanziması
• Geçiş durumu
• Diels-Alder
• Thermal özellikler

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