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The structures of some iminium salts. Crystal structures and13C NMR studies of 3-aryl-2-propenylideniminium salts

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Abstract

The X-ray crystal structures ofE-N, N-dimethyl-3-phenyl-2-propenylideniminium perchlorate,1, andE-N, N-dimethyl-3-(p-methoxyphenyl)-2-propenylideniminium perchlorate,2, have been determined.E-N,N-dimethyl-3-phenyl-2-propenylideniminium perchlorate, (C11H14N+)(ClO4 −),1, is orthorhombic:Pmcn (No. 62)a=6.595(1),b=18,288(4),c=10.216(2) Å,Z=4.E-N, N-dimethyl-3-(p-methoxyphenyl)-2-propenylideniminium perchlorate, (C12H16NO+)(ClO4 −),2, is triclinic:P1 (No. 2) with cell dimensionsa=6.862(1),b=9.830(2),c=13.376(3) Å,α=119.05(1),β=114.99(2), γ=90.79(2)°, andZ=2. Data for both crystals were collected with the use of MoKα radiation and a Syntex P21 diffractometer. The crystal structures were solved by standard methods and refined toR 1=0.0688,R 2=0.0772 for1 andR 1=0.0790 andR 2=0.0757 for 2 based on 869 and 1765 independent reflections, respectively. The bond distances are consistent with a highly localized structure with the positive charge situated principally in the iminium moiety. The13C NMR spectra of these salts were obtained on the crystalline solids by CPMAS methods. Since the13C chemical shifts of the salts were very similar, in both solution and solid states, it was concluded that the structures of the salts were comparable in both phases and were analogous.

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Authors and Affiliations

  1. Department of Chemistry, McMaster University, L8S 4M1, Hamilton, Ontario, Canada

    Ronald F. Childs, Brian D. Dickie, Romolo Faggiani, Colin A. Fyfe, Colin J. L. Lock & Roderick E. Wasylishen

  2. Guelph Waterloo Center for Graduate Work in Chemistry, Guelph University, N1Q2W1, Guelph, Ontario, Canada

    Ronald F. Childs, Brian D. Dickie, Romolo Faggiani, Colin A. Fyfe, Colin J. L. Lock & Roderick E. Wasylishen

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  1. Ronald F. Childs
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Childs, R.F., Dickie, B.D., Faggiani, R. et al. The structures of some iminium salts. Crystal structures and13C NMR studies of 3-aryl-2-propenylideniminium salts. Journal of Crystallographic and Spectroscopic Research 15, 73–87 (1985). https://doi.org/10.1007/BF01185719

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  • DOI: https://doi.org/10.1007/BF01185719

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