Preparation and crystal structures of new schiff bases derived from ۳, ۳ʹ-dihydroxy-۴, ۴ʹ-(propane-۱, ۲-dieloxy)-dibenzaldehyde

In this research study, two Schiff base compounds AP-DHPDB (۱) synthesized from the reaction of ۲-aminophenol (AP) with ۳, ۳ʹ-dihydroxy-۴, ۴ʹ-(propane-۱, ۲-dieloxy)-dibenzaldehyde (DHPDB) and FA-DHEDB (۲) synthesized from the reaction of furfuryl amine (FA) with ۳, ۳ʹ-dihydroxy-۴, ۴ʹ-(ethane-۱, ۲-dieloxy)-dibenzaldehyde (DHEDB) by reflux in methanol as solvent for ۲ h. Suitable crystals of ۱ and ۲ get by slow evaporation of solvent after few days and characterized by elemental analysis. Crystal structures of the title compounds ۱ and ۲ were determined using the single crystal X-ray diffraction analysis. The title compounds ۱ and ۲ were found to be in monoclinic and orthorhombic with the space group of C۲/c and Pnca, respectively. The unit cell parameter of ۱ were a=۲۹/۸۹۹۴(۱۰), b=۴.۸۶۶۱۸(۷), c=۲۱.۷۲۱۴(۴) Å, b=۱۲۴.۴۹۰۱(۱۷)° and V=۲۶۰۴.۸۵(۱۲) Å۳, and the unit cell parameter of ۲ were a=۲۲/۳۵۱۳(۷), b=۲۶.۰۲۵۰(۷), c=۴.۶۶۸۱(۹) Å and V=۲۷۱۵(۱۲) Å۳. The C-N bond distances around the iminic nitrogen of compound ۱ are ۱.۴۱۸ and ۱.۲۶۸ Å, and in compound ۲ are ۱.۴۶۷ and ۱.۲۶۹ Å, indicated the single and double bonds, respectively. Also, the bond angles around the iminic nitrogen are distorted from ۱۲۰° corresponding to sp۲ hybrid (N۱-C۷-C۸ = ۱۲۲.۵° and C۶-N۱-C۷ = ۱۱۹.۳° for ۱ and N۷-C۸-C۹ = ۱۲۳.۹° and C۶-N۷-C۸ = ۱۱۶.۱۲° for ۲).

Keywords:

Schiff base , Aminophenol , Dibenzaldehyde , Furfuryl amine , Monoclinic , Orthorhombic