ABSTRACTMSc. ThesisTHE SYNTHESIS AND PROPERTIES OF N-COORDINATED METALCOMPLEXESNeslihan ŞahinInönü ÜniversityGraduate School of Natural and Applied SciencesDepartment of Chemistry88 + xiii pages2005Supervisor: Assoc. Prof. Dr. smail ÖzdemirDue to catalytic activity toward the various organic reactions and biologic activesubstrats, N-coordinated transition metal complexes have been the subject of numereousresearch.In this concept, firstly 1-substituted imidazoline (1) and benzimidazole (2) wereprepared and their structure was elucidated by mean of spectroscopy.RRNNNN1 2a R= CH2CH2N(Pri)a R= CH2CH2OCH2CH3b R= CH2CH2N(C5H10)b R= CH2CH2N(C5H10)c R= CH2CH2N(C4H8O)c R= CH2CH2N(C4H8O)e R= CH2CH2N(C4H8O) d R= C6H2CH2(OCH3)3-3,4,5e R= CH2(C10H7)iiiStarting from the structurally known compounds, 1-substituted three novel 1-alkylimidazolineruthenium(II) (3-5), and three 1-alkylimidazolinepalladium(II) (6-8)were synthesized.NNOC2H5 ClClClRu N NN NRuN NRuClClCl543N NN O ClCl ClN NPd N NPhMe2PPdPd N NCl Cl2 Cl26 87Novel six compounds 1-alkylbenzimidazoleruthenium(II) (9-15) weresynthesized from 1-substitutedbenzimidazoles, and also three 1-alkylbenzimidazolepalladium(II) (16, 17) were synthesized.N N ON Cl ClClRu N N Ru N NRu N NCl ClCl9 10 11OCH3OCH3OCH3 NClClClN NRuRu N NRu N NClClCl12 1413OCH3 OCH3OCH3 OCH3OCH3 OC3ClNCl Cl PhMe2PPd N NPd N NN NRuClCl Cl21715 16FT-IR, 1H-NMR, 13C-NMR and elementel analysis were used as techniques toelucidiate the structure of the prepared compounds.The catalytic activity of 1-substitutedimidazoline and benzimidazole complexesof 7, 8, 16, 17 in the Heck and Suzuki coupling reactions which were extremelyimportant in organic synthesis. And for the C-C bond formation, the catalysts showedhigh efficiency.KEYWORDS: Azole complexes, imidazoline, benzimidazole, Heck and Suzukicoupling, palladium-imidazoline, ruthenium-imidazoline, palladium-benzimidazole, ruthenium-benzimidazole.iv.

ÖZETYüksek Lisans TeziN-KOORD NE METAL KOMPLEKSLER N N SENTEZveÖZELL KLERNeslihan ŞAH Nnönü ÜniversitesiFen Bilimleri EnstitüsüKimya Anabilim Dalı88 + xiii sayfa2005Danışman: Doç. Dr. smail ÖZDEM RN-Koordine geçiş metal kompleksleri değişik organik tepkimeleri katalizlediklerindenve biyolojik olarak aktif maddeler oldukları için ilgi ile araştırılmaktadır.Çalışma kapsamında öncelikle 1-sübstitüye imidazolin (1) ve benzimidazol (2)sentezlenerek yapıları spektroskopik yöntemlerle belirlendi.RRNNNN1 2a R= CH2CH2N(Pri)a R= CH2CH2OCH2CH3b R= CH2CH2N(C5H10)b R= CH2CH2N(C5H10)c R= CH2CH2N(C4H8O)c R= CH2CH2N(C4H8O)e R= CH2CH2N(C4H8O) d R= C6H2CH2(OCH3)3-3,4,5e R= CH2(C10H7)Yapısı bilinen bu bileşiklerden, 1-sübstitüye imidazolin, yeni üç tane 1-alkilimidazolinrutenyum(II) (3-5) ve üç tane 1-alkilimidazolinpalladyum(II) (6-8) sentezlendi.iNNOC2H5 ClClClRu N NN NRuN NRuClClCl543N NN O ClCl ClN NPd N NPhMe2PPdPd N NCl Cl2 Cl26 871-sübstitüyebenzimidazollerden yeni altı tane 1-alkilbenzimidazolrutenyum(II) (9-15)ve üç tane 1-alkilbenzimidazolpalladyum(II) (16, 17) sentezlendi.N N ON Cl ClClRu N N Ru N NRu N NCl ClCl9 10 11OCH3OCH3OCH3 NClClClN NRuRu N NRu N NClClCl12 1413OCH3 OCH3OCH3 OCH3OCH3 OC3ClNCl Cl PhMe2PPd N NPd N NN NRuClCl Cl21715 16Hazırlanan bu bileşiklerin yapıları FT-IR, 1H-NMR, 13C-NMR ve elementel analiz ileaydınlatıldı.Ayrıca 1-sübstitüyeimidazolin ve benzimidazol komplekslerinden dört tanesinin (7, 8,16, 17) organik kimyada önemli olan, Heck ve Suzuki eşleşme tepkimelerinde katalitiközellikleri incelendi. Bu katalizörlerin belirtilen C-C bağ oluşum tepkimelerinde etkinkatalizörler olduğu saptandı.ANAHTAR KEL MELER: Azol kompleksleri, imidazolin, benzimidazol, Heck ve Suzukieşleşmeleri, paladyum-imidazolin, rutenyum-imidazolin,paladyum-benzimidazol, rutenyum-benzimidazol.ii.