2,3-diaminosuksinik asit ve vic-dioksimli türevlerinin sentezi ve kompleks yapılarının incelenmesi

Abstract

ÖZET Doktora Tezi 2,3-DİAMİNOSUKSİNİK ASİT VE v/c-DİOKSİMLİ TÜREVLERİNİN SENTEZİ VE KOMPLEKS YAPILARININ İNCELENMESİ Ahmet KAHRAMAN Selçuk Üniversitesi Fen Bilimleri Enstitüsü Kimya Anabilim Dalı Danışman: Prof. Dr. Gazi İREZ 1999, 112 Sayfa Jüri: Prof. Dr. Gazi İREZ Prof. Dr. Tevfik GEDİKBEY Prof. Dr. Mehmet SEZGİN Doç. Dr. H- İsmet UÇAN Doç. Dr. İbrahim KARATAŞ Bu çalışmada, iki amino asit ile bunlara ait altı adet yeni vic-dioksimli amino asit ligandı ve bunların bazı geçiş metalleri ile kompleksleri sentezlendi. Bu iki amino asitten biri, 2,3-diamino-3-karbamil propanoik asit, literatürde bulunmayıp orijinal olarak, diğeri 2.3-diaminosuksinik asit literatüre göre sentezlendi. Yeni vic-dioksimli amino asitler; Na.Np-bis(glioksim)-2,3-diaminosuksinik asit, Na,Np-bis(fenilglioksim)-2,3-diaminosuksinik asit, 5,6-bis(hidroksimino>- piperazin-2,3-dikarboksilli asit, Na.Np-bis(glioksim)-2,3-diamino-3-karbamil propanoik asit, Na,Np-bis(fenilglioksim)-2.3-diamino-3-karbamil propanoik asit ve 3 -karbamil-5,6-bis(hidroksimino)piperazin-2-karboksilli asittir. Çalışmanın birinci kademesinde, m eso 2,3-dibromosuksinik asit kullanılarak, orijinal yeni bir amino asit olan 2,3-diamino-3-karbamil propanoik asit sentezlendi. Çalışmanın ikinci kademesinde, meso-2,3-diaminosuksinik asit ve 2,3- diamino- 3-karbamil propanoik asidin anti-klorglioksim, anti-klorfenilglioksim, anti- diklorglioksim ile reaksiyonları sonucu vic-dioksimli amino asit ligandları sentezlendi. Çalışmanın üçüncü kademesinde, belirtilen ligandların Ni(II), Cu(II) ve Pd(II ) iyonları ile vic-dioksim kompleksleri ve biuret kompleksleri izole edildi.Sentezlenen orijinal amino asit altı vic-dioksimli amino asit ligandları ve komplekslerinin yapıları elementel analiz, İR, 'H-NMR spektroskopisi teknikleri ile aydınlatıldı. Anahtar Kelimeler: 2,3-diaminosuksinik asit, 2.3-diamino-3-karbamil propanoik asit 5,6-bis(hidroksimino)piperazin-2,3-dikarboksilli asit, 3-karbamil- 5,6-bis(hidroksimino)piperazin-2-karboksilli asit, vic-dioksim.

ABSTRACT PhD Thesis THE INVESTIGATION OF THE SYNTHESIS OF 2,3-DIAMINOSUCCINIC ACID AND ITS WITH vic-DIOXIMES DERIVATIVES AND ITS TRANSITION METAL'S COMPLEXES Ahmet KAHRAMAN Selçuk University Graduate School of Natural and Applied Sciences Department of Chemistry Supervisor: Prof. Dr. Gazi İREZ 1999, 112 Page Jury: Prof. Dr. Gazi İREZ Prof. Dr. Tevfik GEDİKBEY Prof. Dr. Mehmet SEZGİN Assoc. Prof. Dr. H. İsmet UÇAN Assoc. Prof. Dr. İbrahim KARATAŞ In this study, two amino acids and the derivatives of these are six novel amino acid ligands with v/c-dioxime and their transition metals' complexes were synthesized. One of them, which is 2,3-diamino-3-carbamoyl propanoic acid that's an amino acid has not been reported in the literature previously. That was synthesized originally. The other one is 2,3-diaminosuccinic acid and was synthesized according to the literature. These amino acids with v/c-dioxime have not been reported in the literature previously are Na,Np-bis(glyoxime)-2,3-diaminosuccinic acid, Na,Np-bis(phenyl- glyoxime)-2,3-diaminosuccinic acid, 5,6-bis(hydroxyimino)piperazine-2,3- dicarboxylic acid, Na,Np-bis(glyoxime)-2,3-diamino-3-carbamoyl propanoic acid, Na,Np-bis(phenylglyoxime)-2,3-diamino-3-carbamoyl propanoic acid and 3-carbamoyl -5,6-bis(hydroxyirnino)piperazine-2-carboxylic acid. In the first step of this study, a new amino acid that is 2,3-diamino-3- carbamoyl propanoic acid was synthesized by using /ncyo-2,3-dibromosuccinic acid. In the second step of this study, six novel amino acid ligands with vie-dioximes were synthesized that are anti-chloroglyoxime, anti-chlorophenylglyoxime, anti-dichloroglyoxime derivatives of /weso-2,3-diaminosuccinic acid and 2,3- diamino-3 -carbamoyl propanoic acid. In the third step of this study, biuret and vic-dioxime complexes have been isolated with solution of Ni(II), Cu(II), Pd(II) of indicated ligands. In conclusion, a new original amino acid, six novel amino acid ligands with v/c-dioxime and their complexes were isolated. Their structures were determined by elemental analysis, !H-NMR and IR spectroscopy. Key words: 2,3-diaminosuccinic acid, 2,3 -diamino-3 -carbamoyl propanoic acid, 5,6-bis(hydroxyimino)piperazine-2,3-dicarboxylic acid, 3-carbamoyl-5,6- bis(hydroxyimino)piperazine-2-carboxylic acid, vic-dioxime.