Abstract
The solution v(N-H) vibrations of various disubstituted ureas containing a halophenyl group have been examined in order to directly confirm the presence of an intramolecular NH···Cl hydrogen bond in the o-chloro analog. In chlorophenyl derivatives the v(N-H) band for the N-H bond adjacent to an o-chlorophenyl group is always lower than that for a N-H bond adjacent to a phenyl, m- or p-chlorophenyl group. The corresponding band in N-o-halophenyl- N'-phenylureas, o-XPhUPh [U = HNC(O)NH], shifts to significantly lower wavenumber with increasing atomic size or weight of halogen. The o-XPhUPh derivatives are concluded to be in two intramolecularly NH···X hydrogen-bonded forms with N-H trans or cis to the CO group.
Published Version
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