The synthesis and characterization of a new (E, E)-dioxime, its complex formations of the macrobicyclic group, and conformational analysis of the ligands


DİLBER G. , KANTEKİN H. , YAYLI N. , ABBASOGLU R.

JOURNAL OF COORDINATION CHEMISTRY, cilt.64, ss.3679-3692, 2011 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 64 Konu: 21
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1080/00958972.2011.628018
  • Dergi Adı: JOURNAL OF COORDINATION CHEMISTRY
  • Sayfa Sayıları: ss.3679-3692

Özet

In this study, 19-nitro-6,7,15,16,23,24-hexahydro-13H,26H-14,25-propanotribenzo-[b,i,o] [1,4,11,14,7,18] tetraoxadiazacycloicosine (3) was synthesized using 6,7,8,9,10,11,17,18-octahydro-5H-dibenzo[e,n][1,4]dioxa[8,12]diazacyclopentadesine (1) and 4-nitro-1,2-bis(2-iodoethoxy) benzene (2) as the starting compounds. Macrobicyclic amine 4 was synthesized by reaction of an aromatic nitro compound with hydrazine hydrate (100%) and palladium (10%)-activated carbon in n-butanol. N-1,N-2-di-6,7,15,16,23,24-hexahydro-13H, 26H-14,25-propanotribenzo [b, i, o][1,4,11,14,7,18]tetraoxadiazacycloicosin-19-yl-N'(1),N'(2)-dihydroxyethane-diimidamide vic-dioxime (6) was synthesized by reaction of cyanogen-di-N-oxide in CH2Cl2, which was obtained from (E, E)-dichloroglyoxime and an aqueous solution of Na2CO3 (0.1 N) with 4. Mononuclear Ni(II), Co(III), and Cu(II) complexes, 7, 9, and 10, were synthesized by reaction of vic-dioxime with NiCl2 center dot 6H(2)O, CoCl2 center dot 6H(2)O, and CuCl2 center dot 2H(2)O, respectively. BF2+-Capped mononuclear Ni(II) complex 8 was synthesized by reaction of boron-trifluoride diethyl etherate with mononuclear nickel(II) complex 7 in acetonitrile. The structures of new compounds were determined by elemental analysis, H-1-NMR, C-13-NMR, IR, mass spectroscopic data, and thermal methods (TG/DTA). The conformational analysis of the ligands was performed using DFT and AM1 methods.