Two Schiff Base Ligands Derived from 2,2-Dimethyl-1,3-propanediamine

Abstract

The crystal structures of 2,2'-[2,2-dimethyl-1,3-propanediylbis(nitrilopropylidyne)]diphenol, C23H30N202, and 2, 2' -{ 2, 2-dimethyl -1,3 -propanediylbi s [ nitrilo (phenyl) -methylidyne]}diphenol,

Steric Modification of the Intramolecular Hydrogen Bond in 2-(Methylimino-phenyl-methyl)-phenols

“…Searching in the crystallographic base data set did not show structures directly related to those discussed here, but revealed three structures [11] which can be discussed with respect to an in¯uence of substituents on the properties of the hydrogen bond: 4-((4-chlorophenyl)-(5-¯uoro-2-hydroxyphenyl)-methyleneamino)-butanamide [12], 2,2 H -(2,2-dimethyl-1,3-propanediyl-bis-(nitrilophenylmethylidene))-diphenol [13], and 2,2 H -((1,2-ethanediyl)-bis-(nitrilo-(phenyl)-methylidyne))-bisphenol [14], all of them containing phenyl substituents in the C=N±C moiety. Similar shortenings of distances and changes of angles as discussed here have been observed for these compounds.…”

2,2′-[(Propane-1,3-diyldinitrilo)bis(phenylmethylidyne)]diphenol

“…There are two strong intramolecular O-H..O hydrogen bonds involving the hydroxyl and imine groups forming S(6) ring motifs (Bernstein et al, 1995). These types of hydrogen bonds are common to some reported molecular structures (Schilf et al, 2007;Fernández et al, 2001;Kabak, 2003;Wojciechowski et al, 2001;Dey et al, 2001;Koşar, et al, 2004;Lu, et al, 2008;Qiu & Zhao, 2008;Montazerozohori et al, 2009;Corden et al, 1996). In the crystal structure, weak intermolecular C-H•••O hydrogen bond connect molecules to form a two-dimensional network.…”

“…The title compound forms part of the group of Schiff bases with a similar method of synthesis as described in Schilf et al (2007). The intermolecular hydrogen bonds O-HÁ Á ÁN between the hydroxy and imine are common to this type of compound as shown with the series of compounds reported by Ferná ndez et al (2001); Kabak (2003); Wojciechowski et al (2001); Dey et al (2001); Koşar, et al (2004); Lu, et al (2008); Qiu & Zhao (2008); Montazerozohori et al (2009); Corden et al (1996). For a decription of hydrogen-bond motifs, see: Bernstein et al (1995).…”

N,N′-Bis[(2-hydroxyphenyl)(phenyl)methylidene]propane-1,2-diamine

“…This causes the dihedral angles between the adjacent phenyl rings and phenyl containing plains to be (C1-C6-C7-C8) 89.8 (2)° and (C17-C22-C23-C24) 87.8 (2)° respectively. These dihedral angles are comparable to (Corden et al, 1996) and (Black et al, 2010). The stereogenic centre on the methyl substituted carbon C15 allows the system to pack in the noncentrosymmetric space group C2.…”

“…The molecular structure of the title compound form two strong intermolecular hydrogen bonds O-H•••N involving the hydroxyl and the imine groups, forming S(6) ring motifs which are common to this type of compound (Schilf et al, 2007) and (Fernández-G et al, 2001), and also seen in the work completed by (Kabak et al, 2003), (Wojciechowski et al, 2001), (Dey et al, 2001), (Koşar, et al, 2004), (Lu, et al, 2008) (Qiu & Zhao, 2008), (Montazerozohori et al, 2009, (Corden et al, 1996) and (Black et al, 2010). This causes the dihedral angles between the adjacent phenyl rings and phenyl containing plains to be (C1-C6-C7-C8) 89.8 (2)° and (C17-C22-C23-C24) 87.8 (2)° respectively.…”