Flash vacuum pyrolysis of sulfamoyl azides and chlorides: Facile gas-phase generation of transient N-sulfonylamines

Add time:07/31/2019    Source:sciencedirect.com

Two sulfamoyl azides, H2NS(O)2N3 and MeN(H)S(O)2N3, have been isolated as neat substances and characterized. The solid-state structure of the parent molecule H2NS(O)2N3 has been established with X-ray crystallography. The thermal decomposition of both azides has been studied by combining flash vacuum pyrolysis (FVP, 400 °C) and matrix-isolation IR spectroscopy. In addition to the complete dissociation fragments for H2NS(O)2N3 (SO2, N2, and H2) and MeN(H)S(O)2N3 (SO2, N2, and CH2NH), the retro-ene decomposition products HN3 and N-sulfonylamines HNSO2 and MeNSO2 form, respectively. Alternatively, quantitative yield of both N-sulfonylamines in the gas phase occurs when sulfamoyl chlorides H2NS(O)2Cl and MeN(H)S(O)2Cl are used as the FVP precursors (400 °C). Consistent with these experimental observations, computational studies on the potential energy profiles for the decomposition of the two azides at the CCSD(T)/aug-cc-pVTZ//B3LYP/6-311++G(3df,3pd) level conclusively suggest that the N2-elimination is energetically more favorable than the HN3-elimination through either retro-ene reaction or 1,2-elimination. In contrast, the facile HCl-elimination from sulfamoyl chlorides provides a general method for the gas-phase generation of N-sulfonylamines, which were known as transient reactive intermediates in synthetic chemistry.

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