Synthesis of some new oxime compounds and investigation of their properties
Küçük Resim Yok
Tarih
2005
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Ege Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
V ÖZET BAZI YENİ OKSİM BİLEŞİKLERİNİN SENTEZİ VE ÖZELLİKLERİNİN İNCELENMESİ BABAHAN, İlknur Doktora Tezi, Kimya Anabilim Dalı Tez Yöneticisi: Prof. Dr. Hüseyin ANIL Eylül, 2005, 142 sayfa Bu çalışmada hidrazonların, tiyosemikarbazonların ve semikarbazonların literatürde bulunmayan oksimli türevleri sentezlenerek, metal ekstraksiyonu ve antibakteriyel özellikleri incelenmiştir. Glioksimhidrazin (GEynin 4-nitroasetofenon, diasetilmonoksim, tereftaldialdehit, 4-metilasetofenon ve metil-2-piridil keton ile sırasıyla reaksiyona girmesi sonucunda literatürde bulunmayan hidrazon grupları taşıyan oksim bileşikleri sentezlenmiştir (L1H2, L2H3, L3H2, L4H2 ve L5H4). Semikarbazithidroklorür ve 4-aminoasetofenon semikarbazon'un anti-kloroglioksim ve (E-E)dikloroglioksim ile reaksiyona girmesiyle literatürde bulunmayan semikarbazon ve semikarbazit gruplan taşıyan v/c-dioksim bileşikleri elde edilmiştir (L6H2, L7H2 ve L8H2). 4-aminoasetofenon tiyosemikarbazon'un anti-kloroglioksimle reaksiyona girmesiyle literatürde bulunmayan tiyosemikarbazonun vic- dioksimli türevi sentezlenmiştir (L9H2). Sentezlenen bütün bileşiklerinVI yapısı 1H-NMR, 13C-NMR, HMQC, IR ve elementel analiz teknikleri ile aydınlatılmıştır. Ligantların kompleksleşme özellikleri katı-sıvı ve sıvı-sıvı ekstraksiyonu ile incelenmiştir. Geçiş metallerinin (Ni2+, Cu2+, Co2+, Fe3+, Cr2+, Ag1+ ve Pb2+) ligantlarla (L1H2, L2H3, L3H2, L4H2, L5H4, L6H2, L7H2, L8H2 ve L9H2) ve pikrat iyonları ile organik faza geçişi 25 °C'de UV spektroskopi ile incelenmiştir. Ligantların bütün geçiş metallerine karşı yüksek oranda aktiflik gösterdiği gözlenmiştir. Ligantların (L1H2, L2H3, L3H2, L4H2, L5Ua, L6H2, L7H2, L8H2 ve L9H2) yapısında bulunan oksim ve karbonil gruplarının faz transferinde etkin rol oynadığı düşünülmektedir. Ayrıca yüksek aktiflik gösteren ligantlardaki yumuşak donör azot atomları ligantların ekstraksiyon kapasitelerinin artmasına sebep olmuştur. Ligantların geçiş metalleri ile ekstraksiyonunda etkili bir ekstraktant olmalarına rağmen seçici olmadıkları görülmüştür. Ligantların antibakteriyel özelliklerini incelemek için farklı organizmalara karşı laboratuar koşullarında test edilmişlerdir. Bu amaçla gram pozitif bakterilerden Staphylococcus aureus ATCC 25923, gram negatif bakterilerden ise Escherichia coli ATCC 35218 kullanılmıştır. L3H2, L4H2, L5H4, L7H2 ve L8H2 ligantları antibakteriyel aktiviteye sahip değilken, L1^, L2H3, L6H2 ve L9H2 ligantlarının gram pozitif bakterilerden Staphylococcus aureus ATCC 25923'a karşı antibakteriyel etki gösterdiği tesbit edilmiştir. Anahtar sözcükler: Oksim, v/odioksim, hidrazon, semikarbazon, tiyosemikarbazon, ekstraksiyon, antibakteriyel
VII ABSTRACT SYNTHESIS OF SOME NEW OXIME COMPOUND AND INVESTIGATION OF THEIR PROPERTIES BABAHAN, İlknur Ph. D. Thesis in Chemistry Supervisor: Prof. Dr. Hüseyin ANIL September, 142 pages In this thesis, novel oxime ligands, bearing hydrazone, thiosemicarbazone and semicarbazone side groups which have not been described in the literature previously were synthesized and investigation of metal extraction and antibacterial properties. The oxime ligands of bearing hydrazone side groups (L H2, L H3, L3H2, L4H2 and L5H4) which have not been described in the literature previously were synthesized by reacting anft'-glyoximehydrazine (GH2) with 4-nitroacetophenone, diacetylmonoxime, 4-methylacetophenone, methyl-2-pyridiyl ketone, terephthaldialdehyde respectively. The vz'c-dioxime compounds of bearing semicarbazone side groups (L6H2, L7H2 and L8H2) which have not been described in the literature previously were synthesized by reacting semicarbazide hydrochloride, 4- aminoacetophenone semicarbazone with anfr'-chloroglyoxime and (E,E)- dichloroglyoxime. The other v/c-dioxime compound bearing thiosemicarbazone side group (L9H2) which has not been described in the literature was synthesized by reacting 4-aminoacetophenoneVIII thiosemicarbazone with arcft'-chloroglyoxime. All new compounds were characterized by a combination of lH NMR, 13C NMR, HMQC, IR, and elemental analytical techniques. Their complexing properties were studied by the liquid-liquid and solid-liquid extraction. The extraction of some transition metal cations (Ni2+, Cu2+, Co2+, Fe3+, Cr2+, Ag1+ and Pb2+) by L1H2, L2H3, L3H2, L4H2, L5H4, L6H2, L7H2, L8H2 and L9H2 with picrate anion into organic phase has been studied at 25 °C and UV-visible spectroscopy. It has been observed that ligands show a high affinity to all transition metal cations. The precence of oxime groups and carbonyl groups for L1H2, L2H3; L3H2, L4H2, L5H4, L6H2, L7H2, L8H2 and L9H2 indicate that the oxime groups and carbonyl groups play an important role in the extraction process. The precense in the ligands of soft donor nitrogen groups, which show high affinity to transition metals, causes the increase in the extraction ability of these ligands. It was observed that compounds are effective extractants but not selective at extracting transition metal cations. The ligands have been prepared and tested in vitro against different microorganisms in order to assess their antibacterial properties. For this reason were used Staphylococcus aureus ATCC 25923 from Gram- positive bacteria; Escherichia coli ATCC 35218 from Gram-negative bacteria. The results reveal that L3H2, L4H2, L5FLt, L7H2 and L8H2 have no antimicrobial activity but of which L1^, L2Ü3, L6H2 and L9H2 showed antibacterial activities against Staphylococcus aureus ATCC 25923 from Gram-positive bacteria. Keywords: Oxime, v/c-dioxime, hydrazone, semicarbazone, thiosemicarbazone, extraction, antibacterial.
VII ABSTRACT SYNTHESIS OF SOME NEW OXIME COMPOUND AND INVESTIGATION OF THEIR PROPERTIES BABAHAN, İlknur Ph. D. Thesis in Chemistry Supervisor: Prof. Dr. Hüseyin ANIL September, 142 pages In this thesis, novel oxime ligands, bearing hydrazone, thiosemicarbazone and semicarbazone side groups which have not been described in the literature previously were synthesized and investigation of metal extraction and antibacterial properties. The oxime ligands of bearing hydrazone side groups (L H2, L H3, L3H2, L4H2 and L5H4) which have not been described in the literature previously were synthesized by reacting anft'-glyoximehydrazine (GH2) with 4-nitroacetophenone, diacetylmonoxime, 4-methylacetophenone, methyl-2-pyridiyl ketone, terephthaldialdehyde respectively. The vz'c-dioxime compounds of bearing semicarbazone side groups (L6H2, L7H2 and L8H2) which have not been described in the literature previously were synthesized by reacting semicarbazide hydrochloride, 4- aminoacetophenone semicarbazone with anfr'-chloroglyoxime and (E,E)- dichloroglyoxime. The other v/c-dioxime compound bearing thiosemicarbazone side group (L9H2) which has not been described in the literature was synthesized by reacting 4-aminoacetophenoneVIII thiosemicarbazone with arcft'-chloroglyoxime. All new compounds were characterized by a combination of lH NMR, 13C NMR, HMQC, IR, and elemental analytical techniques. Their complexing properties were studied by the liquid-liquid and solid-liquid extraction. The extraction of some transition metal cations (Ni2+, Cu2+, Co2+, Fe3+, Cr2+, Ag1+ and Pb2+) by L1H2, L2H3, L3H2, L4H2, L5H4, L6H2, L7H2, L8H2 and L9H2 with picrate anion into organic phase has been studied at 25 °C and UV-visible spectroscopy. It has been observed that ligands show a high affinity to all transition metal cations. The precence of oxime groups and carbonyl groups for L1H2, L2H3; L3H2, L4H2, L5H4, L6H2, L7H2, L8H2 and L9H2 indicate that the oxime groups and carbonyl groups play an important role in the extraction process. The precense in the ligands of soft donor nitrogen groups, which show high affinity to transition metals, causes the increase in the extraction ability of these ligands. It was observed that compounds are effective extractants but not selective at extracting transition metal cations. The ligands have been prepared and tested in vitro against different microorganisms in order to assess their antibacterial properties. For this reason were used Staphylococcus aureus ATCC 25923 from Gram- positive bacteria; Escherichia coli ATCC 35218 from Gram-negative bacteria. The results reveal that L3H2, L4H2, L5FLt, L7H2 and L8H2 have no antimicrobial activity but of which L1^, L2Ü3, L6H2 and L9H2 showed antibacterial activities against Staphylococcus aureus ATCC 25923 from Gram-positive bacteria. Keywords: Oxime, v/c-dioxime, hydrazone, semicarbazone, thiosemicarbazone, extraction, antibacterial.
Açıklama
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Anahtar Kelimeler
Kimya, Chemistry