Synthesis and spectroscopic characterization of asymmetric Schiff bases derived from 4′-formylbenzo-15-crown-5 containing recognition sites for alkali and transition metal guest cations

作者: Zeliha Hayvali , Didem Yardimci

DOI: 10.1007/S11243-008-9060-4

关键词: Crown CompoundsOrganometallic chemistryChemistryPolymer chemistryInorganic chemistrySchiff baseMetal salen complexesCrown etherLigand15-Crown-5Salicylaldehyde

摘要: Asymmetric salen-type Schiff base ligands have been synthesized via a stepwise approach. In the first step, mono-Schiff compounds were prepared by condensation of salicylaldehyde, 2-hydroxy-3-methoxybenzaldehyde, 2-hydroxy-5-methoxybenzaldehyde and 2-hydroxy-1-naphthaldehyde with hydrazine hydrate. These then reacted 4′-formylbenzo-15-crown-5 to prepare asymmetric ligands. 1H-NMR spectra indicate that mono- bis-Schiff exist in both (E) (Z) isomeric forms CDCl3 solution. The crown form crystalline 1:1 (Na+:ligand) complexes sodium perchlorate. Homo-metallic Ni(II) Zn(II) 1:2 (metal:ligand) stoichiometries also synthesized. results coordinate through azomethine nitrogen phenolic oxygen.

参考文章(31)
Zeliha Hayvali, Mustafa Hayvali, Zeynel Kiliç, Tuncer Hökelek, Edwin Weber, New Benzo-15-Crown-5 Ethers Featuring Salicylic Schiff Base Substitutions – Synthesis, Complexes and Structural Study Journal of Inclusion Phenomena and Macrocyclic Chemistry. ,vol. 45, pp. 285- 294 ,(2003) , 10.1023/A:1024568309739
David E. Fenton, Donald Parkin, Roger F. Newton, The synthesis of adrenaline crown ethers Journal of the Chemical Society, Perkin Transactions 1. ,vol. 12, pp. 449- 454 ,(1981) , 10.1039/P19810000449
Carla Sousa, Cristina Freire, Baltazar De Castro, Synthesis and Characterization of Benzo-15-Crown-5 Ethers with Appended N2O Schiff Bases Molecules. ,vol. 8, pp. 894- 900 ,(2003) , 10.3390/81200894
Xianzhi Zhou, Michael D. Toney, pH studies on the mechanism of the pyridoxal phosphate-dependent dialkylglycine decarboxylase. Biochemistry. ,vol. 38, pp. 311- 320 ,(1999) , 10.1021/BI981455S
Xiao-Xia Lu, Sheng-Ying Qin, Zhong-Yuan Zhou, Vivian Wing-Wah Yam, Synthesis, structure, and ion-binding studies of cobalt(II) complexes with aza-crown substituted salicylaldimine Schiff base ligand Inorganica Chimica Acta. ,vol. 346, pp. 49- 56 ,(2003) , 10.1016/S0020-1693(02)01391-9
Edmund Kwiatkowski, Marek Kwiatkowski, Unsymmetrical schiff base complexes of nickel(II) and palladium(II) Inorganica Chimica Acta. ,vol. 42, pp. 197- 202 ,(1980) , 10.1016/S0020-1693(00)88912-4
Dionisia Sanz, María Alejandra Ponce, Rosa María Claramunt, Cristina Fernández-Castaño, Concepción Foces-Foces, José Elguero, SYNTHESIS AND STRUCTURAL STUDIES OF SYMMETRIC AND UNSYMMETRIC ADAMANTYLMETHYLENEAZINES Journal of Physical Organic Chemistry. ,vol. 12, pp. 455- 469 ,(1999) , 10.1002/(SICI)1099-1395(199906)12:6<455::AID-POC146>3.0.CO;2-3
Z. Cimerman, R. Kiralj, N. Galić, The structure and tautomeric properties of 2-(3-pyridylmethyliminomethyl)phenol☆ Journal of Molecular Structure. ,vol. 323, pp. 7- 14 ,(1994) , 10.1016/0022-2860(93)07972-Y