caa a22 4500 463184440 CHVBK 20180406164848.0 cr unu---uuuuu 170326e20071201xx s 000 0 eng 10.1007/s10870-007-9257-y doi (NATIONALLICENCE)springer-10.1007/s10870-007-9257-y Synthesis of O -Alkylbenzohydroximoyl Iodides and a Comparison of their Structures to other Oxime Derivatives [Elektronische Daten] [Debra Dolliver, Smitty Smith, David Delatte, Kavi Patel, Tiffany Thomas, Julie Chagnard, James Johnson, Diana Canseco, Frank Fronczek, Clinton Bryan, JoAnn Muller, Jeffrey Rowe, Artie McKim] 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)Å, b=6.5217(15)Å, and c=11.755(2)Å, and p-ClArC(I)=NOCH3 crystallizes in space group P21/n with lattice constants a=15.670(4)Å, b=5.742(4)Å, and c=27.156(7)Å 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)Å, b=22.501(5)Å, and c=10.088(2)Å 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)Å, b=7.0774(10)Å, and c=12.2741(15)Å 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)Å, b=11.310(3)Å, and c=7.351(2)Å 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. Springer Science+Business Media, LLC, 2007 Imidoyl iodide nationallicence Imidoyl azide nationallicence N -alkoxyimine nationallicence N -alkoxyimidoyl halide nationallicence Oxime thioether nationallicence Thiohydroximate nationallicence Dolliver Debra Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut Smith Smitty Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut Delatte David Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut Patel Kavi Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut Thomas Tiffany Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut Chagnard Julie Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut Johnson James Department of Chemistry and Physics, Texas Woman's University, 76201-5859, Denton, TX, USA aut Canseco Diana Department of Chemistry and Physics, Texas Woman's University, 76201-5859, Denton, TX, USA aut Fronczek Frank Department of Chemistry, Louisiana State University, 70803, Baton Rouge, LA, USA aut Bryan Clinton Department of Physical Sciences, Cameron University, 73505, Lawton, OK, USA aut Muller JoAnn Department of Physical Sciences, Cameron University, 73505, Lawton, OK, USA aut Rowe Jeffrey School of Chemistry, La Trobe University, 3086, Bundoora, VIC, Australia aut McKim Artie Gaylord Chemical Company, L.L.C., 70427, Bogalusa, LA, USA aut Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/12(2007-12-01), 837-846 1074-1542 37:12<837 2007 37 10870 https://doi.org/10.1007/s10870-007-9257-y text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10870-007-9257-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Dolliver Debra Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut NATIONALLICENCE 700 1- Smith Smitty Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut NATIONALLICENCE 700 1- Delatte David Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut NATIONALLICENCE 700 1- Patel Kavi Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut NATIONALLICENCE 700 1- Thomas Tiffany Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut NATIONALLICENCE 700 1- Chagnard Julie Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, 70402, Hammond, LA, USA aut NATIONALLICENCE 700 1- Johnson James Department of Chemistry and Physics, Texas Woman's University, 76201-5859, Denton, TX, USA aut NATIONALLICENCE 700 1- Canseco Diana Department of Chemistry and Physics, Texas Woman's University, 76201-5859, Denton, TX, USA aut NATIONALLICENCE 700 1- Fronczek Frank Department of Chemistry, Louisiana State University, 70803, Baton Rouge, LA, USA aut NATIONALLICENCE 700 1- Bryan Clinton Department of Physical Sciences, Cameron University, 73505, Lawton, OK, USA aut NATIONALLICENCE 700 1- Muller JoAnn Department of Physical Sciences, Cameron University, 73505, Lawton, OK, USA aut NATIONALLICENCE 700 1- Rowe Jeffrey School of Chemistry, La Trobe University, 3086, Bundoora, VIC, Australia aut NATIONALLICENCE 700 1- McKim Artie Gaylord Chemical Company, L.L.C., 70427, Bogalusa, LA, USA aut NATIONALLICENCE 773 0- Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/12(2007-12-01), 837-846 1074-1542 37:12<837 2007 37 10870 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer