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Title: Comparison of the structure and charge delocalization in an unsaturated imine and its corresponding iminium salt

Journal Article · · Journal of the American Chemical Society; (USA)
DOI:https://doi.org/10.1021/ja00196a056· OSTI ID:6724145
; ;  [1]
  1. McMaster Univ., Hamilton, Ontario (Canada)

The crystal structures of N-phenyl-3-(p-chlorophenyl)-2-propenimine, 1, and N-methyl-N-phenyl-3-(p-chlorophenyl)-2-propeniminium perchlorate, 2, have been determined by single-crystal x-ray techniques. Both compounds exist as monoclinic crystals, space group P2{sub 1}/c, with four molecules per unit cell. The imine 1 has cell dimensions of a = 14.438 (4) {angstrom}, b = 14.348 (4) {angstrom}, c = 6.240 (2) {angstrom}, and {beta} = 101.57 (3) {degree}. The corresponding iminium salt 2 has cell dimensions of a = 7.811 (2) {angstrom}, b = 16.811 (5) {angstrom}, c = 13.876 (3) {angstrom}, and {beta} = 113.26 (2){degree}. The three-dimensional structures of 1 and 2 are remarkably similar in terms of geometry and bond lengths. The conclusions reached from the crystallographic data have been compared with {sup 13}C NMR spectroscopic data as well as theoretical studies.

OSTI ID:
6724145
Journal Information:
Journal of the American Chemical Society; (USA), Vol. 111:14; ISSN 0002-7863
Country of Publication:
United States
Language:
English