engleski

A Reinvestigation of the Quinoidal Effect in N-n-Propyl-2-oxo-1-naphthylidenemethylamine

In the title compound C14H15NO (systematic name: 1-n-propylaminomethylene-2-naphthalenone), an intramolecular N-H...O hydrogen bond (N...O 257.8(2), N-H 77.5, H...O 193.6 pm) arises when the hydroxyl-H atom of the Schiff base prepared from 2-hydroxy-1-naphthaldehyde and n-propylamine shifts to the N atom. This is the consequence of the pronounced quinoidal effect in the 2-oxo-1-naphthaldimine moiety which has a very short C3=C4 bond of 134.3(3) pm. The spatial orientation of the N-substituent with respect to the rest of the molecule (which is planar) depends on the surroundings of the molecules defined by the crystal packing.

Quinoidal effect; intramolecular hydrogen bond; naphthaldimine Schiff bases

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