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Synthesis of O-Alkylbenzohydroximoyl Iodides and a Comparison of their Structures to other Oxime Derivatives

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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) 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.

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Notes

  1. Supplementary crystallographic data for this paper in CIF format can be obtained, free of charge, via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K. (Fax: 44–1223–336033 or e-mail: deposit@ccdc.cam.ac.uk)

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Acknowledgments

Acknowledgment is made to the State of Louisiana Board of Regents Grant (LEQSF(2006-09)-RD-A-25), Southeastern Louisiana University’s Faculty Development Grant, Southeastern Louisiana University’s OSCAR/STAR Grant, the Minority Biomedical Research Support Program of the National Institutes of Health (NIH-MBRS Grant R25-GM55380), The Robert A. Welch Foundation (Grant No. M-0200) and the Texas Woman’s University Research Enhancement Program for support of this work. The purchase of the KappaCCD diffractometer was made possible by Grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

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Authors and Affiliations

  1. Department of Chemistry and Physics, SLU 10878, Southeastern Louisiana University, Hammond, LA, 70402, USA

    Debra D. Dolliver, Smitty Smith, David B. Delatte, Kavi D. Patel, Tiffany E. Thomas & Julie Chagnard

  2. Department of Chemistry and Physics, Texas Woman’s University, Denton, TX, 76201-5859, USA

    James E. Johnson & Diana C. Canseco

  3. Department of Chemistry, Louisiana State University, Baton Rouge, LA, 70803, USA

    Frank R. Fronczek

  4. Department of Physical Sciences, Cameron University, Lawton, OK, 73505, USA

    Clinton D. Bryan & JoAnn R. Muller

  5. School of Chemistry, La Trobe University, Bundoora, VIC, 3086, Australia

    Jeffrey E. Rowe

  6. Gaylord Chemical Company, L.L.C., Bogalusa, LA, 70427, USA

    Artie S. McKim

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  1. Debra D. Dolliver
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Correspondence to Debra D. Dolliver.

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Dolliver, D.D., Smith, S., Delatte, D.B. et al. Synthesis of O-Alkylbenzohydroximoyl Iodides and a Comparison of their Structures to other Oxime Derivatives. J Chem Crystallogr 37, 837–846 (2007). https://doi.org/10.1007/s10870-007-9257-y

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