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<p>DFT calculation tools were employed to investigate the physical and chemical properties, as well as the reactivity, of dichlorophosphoryl isocyanate towards organoazide substrates. Analysis of the global charge distribution obtained from frontier molecular orbital (FMO) calculations and the local atomic charge distribution derived from Fukui function calculations revealed that 1,4-disubstituted tetrazolin-5-ones are the most stable among the four theoretically possible reaction products. The experimental reaction was conducted in toluene at 80&#xa0;°C, affording the predicted heterocyclic products. Advanced IRC calculations revealed that the reaction proceeds through a two-step mechanism, in contrast to previous literature reports suggesting a concerted mechanism for this class of reactions. By determining the energy values of the super molecular complex (<b>SM</b>), transition states (<b>TS</b>), intermediate states (<b>I</b>), and products, along with the variations in interatomic distances and angles, we were able to understand the evolution of the species during the two reaction steps. The analysis of the molecular structures of the obtained heterocyclic products, including their dipole moments, motivated us to predict their potential ADMET pharmacological properties.</p>

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DFT Calculations, Synthesis, and Mechanistic Studies of the Reaction of Dichlorophosphoryl Isocyanate with Hydrocarbon Azides

  • 期刊论文

  • 发表日期：

    2025年10月24日

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  • Outaf Fliss,
  • Imen Ferchichi,
  • Mohamed Abederrahmene Khouna Sanhoury,
  • Nejib Mekni

摘要

DFT calculation tools were employed to investigate the physical and chemical properties, as well as the reactivity, of dichlorophosphoryl isocyanate towards organoazide substrates. Analysis of the global charge distribution obtained from frontier molecular orbital (FMO) calculations and the local atomic charge distribution derived from Fukui function calculations revealed that 1,4-disubstituted tetrazolin-5-ones are the most stable among the four theoretically possible reaction products. The experimental reaction was conducted in toluene at 80 °C, affording the predicted heterocyclic products. Advanced IRC calculations revealed that the reaction proceeds through a two-step mechanism, in contrast to previous literature reports suggesting a concerted mechanism for this class of reactions. By determining the energy values of the super molecular complex (SM), transition states (TS), intermediate states (I), and products, along with the variations in interatomic distances and angles, we were able to understand the evolution of the species during the two reaction steps. The analysis of the molecular structures of the obtained heterocyclic products, including their dipole moments, motivated us to predict their potential ADMET pharmacological properties.