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Complete solution NMR analysis of three oligoimine model compounds
Author(s) -
Spencer Lynne,
Euler William B.,
Traficante Daniel D.,
Kim Misoo,
Rosen William
Publication year - 1998
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199806)36:6<398::aid-omr315>3.0.co;2-u
Subject(s) - trimer , chemistry , dimer , monomer , steric effects , imine , covalent bond , stereochemistry , crystallography , tetramer , nmr spectra database , proton nmr , nuclear magnetic resonance spectroscopy , computational chemistry , spectral line , polymer , organic chemistry , physics , astronomy , catalysis , enzyme
A series of three model compounds (monomer, dimer and trimer analogues) representing polyisocyanides were synthesized and their solution NMR spectra were characterized. Analysis of the monomer and dimer analogues led to the conclusion that the most stable forms of these molecular systems are planar with the C—C bond in an s ‐ trans conformation and the imine moieties in a Z conformation. In solution, the trimer analogue exhibits a preferred conformation that has a planar s ‐ trans ‐diimine segment covalently attached to a magnetically isolated monoimine segment such that each segment is oriented at approximately 90° to the other. This latter observation gives significant insight into the preferred molecular structure to be expected for sterically unconstrained poly( N ‐phenyliminomethylene) in solution. © 1998 John Wiley & Sons, Ltd.