DFT calculations, microsynthesis and characterization of isopropyl methylphosphonoselenofluoridate [sarin-Se]

Abstract

Isopropyl methylphosphonoselenofluoridate (sarin-Se) was synthesized in order to determine its analytical data and to compare them as well as its reactivity parameters with those of sarin. After synthesis, sarin-Se was characterized using ¹H, ¹³ C and ³¹P NMR spectroscopy and high resolution mass spectrometry (HRMS). ¹H and ¹³ C NMR chemical shifts were also calculated using density functional theory (DFT) and compared with experimental data, showing a close agreement. Electrophilicity indices of sarin and sarin-Se were calculated at B3LYP/6-31++G (2d, 2p) level of theory. HOMO-LUMO analysis provides a basis to explain electrophilic nature of sarin-Se and sarin, which are almost similar. Based on calculated data, ³¹P NMR chemical shift and the reactivity of sarin-Se towards some enzymes such as acetylcholinesterase and albumin were explained.

Graphical Abstract

Keywords:

• Sarin
• sarin-Se
• DFT calculations
• electrophilicity
• HOMO-LUMO analysis
• acetylcholinesterase

Ethical statement

No potential conflict of interest was reported by the authors.