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Synthesis of O-Alkylbenzohydroximoyl Iodides and a Comparison of their Structures to other Oxime Derivatives |
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| Authors: | Debra D. Dolliver Smitty Smith David B. Delatte Kavi D. Patel Tiffany E. Thomas Julie Chagnard James E. Johnson Diana C. Canseco Frank R. Fronczek Clinton D. Bryan JoAnn R. Muller Jeffrey E. Rowe Artie S. McKim | ||
| Affiliation: | 1. Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, Hammond, LA, 70402, USA 2. Department of Chemistry and Physics, Texas Woman’s University, Denton, TX, 76201-5859, USA 3. Department of Chemistry, Louisiana State University, Baton Rouge, LA, 70803, USA 4. Department of Physical Sciences, Cameron University, Lawton, OK, 73505, USA 5. School of Chemistry, La Trobe University, Bundoora, VIC, 3086, Australia 6. Gaylord Chemical Company, L.L.C., Bogalusa, LA, 70427, USA |
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| Abstract: | Abstract The first general synthesis of (Z)-O-alkylbenzohydroximidoyl iodides [ArC(I)=NOR] is reported. X-ray crystallographic structures of two of these compounds confirm that they are in the Z-configuration: p-NO2ArC(I)=NOCH3 crystallizes in space group Pnma with lattice constants a = 12.682(2) ?, b = 6.5217(15) ?, and c = 11.755(2) ?, and p-ClArC(I)=NOCH3 crystallizes in space group P21/n with lattice constants a = 15.670(4) ?, b = 5.742(4) ?, and c = 27.156(7) ? and beta angle 102.71(2). Their structures are compared to other O-alkylbenzohydroximoyl halides including p-NO2ArC(F)=NOCH3 which crystallizes in space group P21/c with lattice constants a = 3.8475(10) ?, b = 22.501(5) ?, and c = 10.088(2) ? and beta angle 91.130(11). The synthesis of two additional compounds containing the N-alkoxyimine moiety {methyl (Z)-O-methyl-4-nitrobenzothiohydroximate [p-NO2ArC(SCH3)=NOCH3] which crystallizes in space group P21/n with lattice constants a = 11.8046(15) ?, b = 7.0774(10) ?, and c = 12.2741(15) ? and beta angle 100.401(9) and (Z)-O-methyl-4-nitrobenzohydroximoyl azide [p-NO2ArC(N3)=NOCH3] which crystallizes in space group P21/c with lattice constants a = 11.753(2) ?, b = 11.310(3) ?, and c = 7.351(2) ? and beta angle 103.805(15) are also reported. Their structures are compared to (Z)-ethyl benzohydroximate [PhC(OEt)=NOH] and (Z)-O-methyl-4-nitrobenzohydroximoyl cyanide [p-NO2ArC(CN)=NOCH3] respectively. Characterizations include spectrometric identifications employing IR, 1H-NMR, 13C-NMR and mass spectrometry. Index Abstract X-ray structures of several N-alkoxyimines, including the newly synthesized N-alkoxyimidoyl iodides and azide, have been performed, and these structures unambiguously show the geometric configuration (E vs. Z) of these compounds. 
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| Keywords: | Imidoyl iodide Imidoyl azide N-alkoxyimine N-alkoxyimidoyl halide Oxime thioether Thiohydroximate | ||
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