Journal of Chemical Crystallography p. 837 - 846 (2007)
Update date:2022-08-05
Topics:
Dolliver, Debra D.
Smith, Smitty
Delatte, David B.
Patel, Kavi D.
Thomas, Tiffany E.
Chagnard, Julie
Johnson, James E.
Canseco, Diana C.
Fronczek, Frank R.
Bryan, Clinton D.
Muller, Joann R.
Rowe, Jeffrey E.
McKim, Artie S.
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) A, b = 6.5217(15) A, and c = 11.755(2) A, and p-ClArC(I)=NOCH3 crystallizes in space group P21/n with lattice constants a = 15.670(4) A, b = 5.742(4) A, and c = 27.156(7) A and beta angle 102.71(2). Their structures are compared to other O-alkylbenzohydroximoyl halides including p-NO2ArC(F)=NOCH 3 which crystallizes in space group P21/c with lattice constants a = 3.8475(10) A, b = 22.501(5) A, and c = 10.088(2) A 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)=NOCH 3] which crystallizes in space group P21/n with lattice constants a = 11.8046(15) A, b = 7.0774(10) A, and c = 12.2741(15) A 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) A, b = 11.310(3) A, and c = 7.351(2) A 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-NO 2ArC(CN)=NOCH3] respectively. Characterizations include spectrometric identifications employing IR, 1H-NMR, 13C-NMR and mass spectrometry.
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