Easy Synthesis and Crystal Structure of a Novel Ortho Hydroxyl Schiff Base Compound CH2-{CYCLO-C6H10)-NCH-C6H4-OH-2}2

Abstract

A one-pot and neat reaction procedure is used for the synthesis of CH₂-{cyclo-C₆H₁₀)-NCH-C₆H₄-OH-2}₂. ¹H NMR shows a mixture of ZE and EE isomers in a ratio of 2:0.9. The EE isomer is easily isolated as crystals suitable for the X-ray analysis. ¹H,¹³C NMR and UV-visible spectra of the title compound are studied in different solvents. The crystal structure shows intramolecular H bonds as an EE isomer. The molecule lies about a twofold symmetry axis, passing through the C1 atom. The cyclo-hexyl ring C2-7 shows a chair conformation, with both C2-C1 and C5-N1 bonds in equatorial orientations. The phenolic hydrogen atom H1a forms a good hydrogen bond with the imino nitrogen atom N1 and the N1-C8 bond is short, as expected for a double bond (1.265(4) Å).