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15N NMR, 1H NOE difference spectroscopy and conformation of N-(o-aminophenyl)-N′-alkylureas

✍ Scribed by Bertrand J. Jean-Claude; George Just

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
505 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^15^N NMR spectra of five N‐(o‐aminophenyl)‐N′ substituted ureas and their hydrochloride salts were recorded in DMSO. N‐1 was more shielded in these ureas than in N‐phenyl‐N′‐methylurea. The shifts of N‐3 varied with the substituents. Proton exchanges at N‐3 were observed when the spectra of the hydrochloride salts were recorded. The preferential trans‐trans orientation of the protons with respect to the carbonyl in the ureido group was confirmed by NOE difference spectroscopy. In the solid, the conformation of N(o‐aminophenyl)‐N′‐methylurea, which was determined by x‐ray diffraction, was found to be similar to the suggested conformation in solution; the ^15^N shifts of this compound in the solid state were determined by ^15^N cross‐polarization magic angle spinning NMR.

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