6533b7d4fe1ef96bd12632bc

RESEARCH PRODUCT

Two (E)-2-({[4-(dialkylamino)phenyl]imino}methyl)-4-nitrophenols.

Kari RissanenArto ValkonenErkki KolehmainenRyszard GawineckiAleksandra GrzegórskaBorys Ośmiałowski

subject

StereochemistryHydrogen bondStackingSpace groupGeneral MedicineCrystal structureStructural differenceRing (chemistry)General Biochemistry Genetics and Molecular BiologyCrystallographychemistry.chemical_compoundchemistryPhenolBenzeneta116

description

The slow evaporation of analytical NMR samples resulted in the formation of crystals of (E)-2-({[4-(dimethylamino)phenyl]imino}methyl)-4-nitrophenol, C15H15N3O3, (I), and (E)-2-({[4-(diethylamino)phenyl]imino}methyl)-4-nitrophenol, C17H19N3O3, (II). Despite the small structural difference between these twoN-salicylideneaniline derivatives, they show different space groups and diverse molecular packing. The molecules of both compounds are close to being planar due to an intramolecular O—H...N hydrogen bond. The 4-alkylamino-substituted benzene ring is inclined at an angle of 13.44 (19)° in (I) and 2.57 (8)° in (II) with respect to the 4-nitro-substituted phenol ring. Only very weak intermolecular π–π stacking and C—H...O interactions were found in these structures.

10.1107/s0108270112025589https://pubmed.ncbi.nlm.nih.gov/22850851