Crystal structure of 2,2'-[(1,4-butylene)dioxybis(nitrilomethylidyne)]- dinaphthol, C26H24N2O4

Abstract

Source of materialToane thanol solution (10 ml) of 2-hydroxy-1-naphthaldehyde (349.5 mg, 2.01 mmol) wasadded anethanol solution (3 ml) of 1,4-bis(aminooxy)butane (120.12 mg, 1.0 mmol). After the solution hadbeen stirred at55°Cfor 4h,the mixture wasfiltered, washed successively with ethanoland ethanol/hexane (1:4), respectively. DiscussionRecently, agreatdealofattention hasfocused on aseriesof N , N ¢ -bis(salicylidene)ethylenediamine (salen) and its derivatives [1,2], because these compounds easily form metallosalenc omplexes and some of them have excellent catalyticactivities for epoxidation, aziridination, etc. [3,4]. Inaddition, they are also used asmodels of reaction centers of metalloenzymes [5,6], and nonlinearopticalmaterials [7]. Moreover,inbiologicaland artificialsystems allosteric regulation is effective in controlling molecularf unctions, such asm olecularr ecognition and biological activity [8]. Totune or improve such functions, chemicalmodifications of abasic salen skeleton is very interesting and important [9][10][11][12]. Sothe introduction of some functionalgroups or substitution of some partswith appropriate ones are effective and inevitable. Some of such compounds have two salicylidene units, but the linkage waslimited to analkylene (-CH = N-C-X-C-N = CH-) group due to the ease of preparation. Ifan O -alkyloxime moiety which is observed for 2-hydroxy-1-naphthaldehyde. The title compound is sufficiently stable to resist scrambling of the C = N bonds. This maybeascribed to lower reactivity of the oxime C = N bonds toward nucleophiles.

Crystal structure of 2,2′-((1,4-butylene)dioxybis(nitrilomethylidyne)) diphenol, C18H20N2O4

“…Thus, we approached the synthesis of anew series of salen-type chelating compoundsonthe basis of O -alkyloxime which canb es table enough to resist the metathesis of the C = Nbonds, because the rate constants of oxime formation are smallerthanthose of imine formation and the equilibrium constants are larger by severalo rders [13]. We have recently reported some O -alkyloxime derivatives of salen [2][3][4]. Inc ontinuation of our previous work, we synthesized a salen-type bisoxime compound and determinedthe crystalstruc- …”

“…The title compound wasprepared by modification of the reported method [1][2][3][4]. Toanethanol solution (10 ml) of salicylaldehyde (245.5 mg, 2.01 mmol) wasadded anethanol solution (3 ml) of 1,4-bis(aminooxy)butane (120.12 mg, 1.0 mmol).…”

Synthesis and Crystal Structure of 4,4',6,6'-Tetrachloro-2,2'-[(1,4-butylene)dioxybis(nitrilmethylidyne)]diphenol

“…Most of their important features of these compounds are their preparative accessibility, diversity and structural variability, which make them more attractive. Some salen-type bisoxime derivatives, such as 2,2'-[(1,4-butylene)dioxybis(nitrilomethylidyne)] dinaphthol 8 15 Key Words: Salen-type bisoxime compound, Synthesis, Crystal structure, Supramolecular interaction. EXPERIMENTAL 2-Hydroxybenzaldehyde was purchased from Alfa Aesar and used without further purification.…”

Crystal Structure of an Unexpected Oxime-Type Polymer (C10H11BrNO)n

“…The synthesis of the title compound was used the similar synthetic route according to previously reported work 4 . However, it is remarkable that it did not form the desired symmetrical bisoxime compound, bis(3-bromobenzaldehyde) O,O'-(hexane-1,6-diyl)dioxime, but obtained a unexpected oxime-type polymer (C10H11BrNO)n, which was formed in the course of the the Schiff base reaction of 3-bromobenzaldehyde and 1,6-bis(aminooxy) hexane.…”