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)
- 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), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:14; ISSN 0002-7863; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400500* -- Photochemistry
550000 -- Biomedical Sciences
Basic Studies
59 BASIC BIOLOGICAL SCIENCES
CALCULATION METHODS
CHEMISTRY
CRYSTAL STRUCTURE
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
IMINES
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHOTOCHEMISTRY
PROTEINS
400500* -- Photochemistry
550000 -- Biomedical Sciences
Basic Studies
59 BASIC BIOLOGICAL SCIENCES
CALCULATION METHODS
CHEMISTRY
CRYSTAL STRUCTURE
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
IMINES
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHOTOCHEMISTRY
PROTEINS