Araştırma Makalesi
PDF EndNote BibTex RIS Kaynak Göster

Kloro[1-Allil-3-(2-diizopropilaminoetil)benzimidazol-2-iliden]gümüş(I)’in sentezi ve yapısal karakterizasyonu

Yıl 2020, Cilt 10, Sayı 2, 66 - 75, 31.12.2020

Öz

N-heterosiklik karben-metal kompleksleri, biyolojik özelliklere sahip olmaları ve organik sentez tepkimelerinde katalizör olarak kullanılmaları nedeni ile koordinasyon kimyasının en önemli çalışma konularından biridir. Bu çalışmada potansiyel katalizör ve biyolojik ajan olabilecek bir yeni benzimidazolyum tuzu ve bu tuzun Ag(I)-NHC kompleksi sentezlendi. Elde edilen her iki yeni bileşiğin yapısı FT-IR, 1H NMR ve 13C{1H} NMR spektroskopileri ile tam olarak karakterize edildi.

Kaynakça

  • Almeida R A, Peixoto F A, Calvete J F M, Gois M P P & Pereira M M (2011). Rhodium (I) N-Heterocyclic carbene complexes as catalysts for hydroformylation of olefins: an overview. Current Organic Synthesis 8(5): 764-775.
  • Arduengo III A J, Harlow R L & Kline M (1991). A stable crystalline carbene [Erratum to document cited in CA114 (7): 62009r]. Journal of the American Chemical Society 113 (7): 2801-2801.
  • Asif M, Iqbal M A, Hussein M A, Oon C E, Haque R A, Ahamed M B K, Khadeer A M B, Majid A A S, Majid A M S A (2016). Human colon cancer targeted pro-apoptotic, anti-metastatic and cytostatic effects of binuclear Silver(I)-N-Heterocyclic carbene (NHC) complexesEur. European journal of medicinal chemistry 108:177-187.
  • Çevik-Yıldız E, Şahin N & Şahin-Bölükbaşı S. (2020). Synthesis, characterization, and investigation of antiproliferative activity of novel Ag (I)-N-Heterocyclic Carbene (NHC) compounds. Journal of Molecular Structure, 1199: 126987.
  • Demirayak Ş, Mohsen U A & Karaburun A Ç (2002). Synthesis and anticancer and anti-HIV testing of some pyrazino [1, 2-a] benzimidazole derivatives. European journal of medicinal chemistry 37 (3): 255-260.
  • Díez-González S, Marion N, Nolan S P (2009). N-heterocyclic carbenes in late transition metal catalysis. Chemical Reviews 109 (8): 3612-3676.
  • Gudmundsson K S, Tidwell J, Lippa N, Koszalka G W, van Draanen N, Ptak R G & Townsend, L. B. (2000). Synthesis and antiviral evaluation of halogenated β-d-and-l-erythrofuranosylbenzimidazoles. Journal of medicinal chemistry 43 (12), 2464-2472.
  • Feller D, Borden W T, Davidson E R (1980). Dependence of the singlet-triplet splitting in heterosubstituted carbenes on the heteroatom electronegativity and conformation. Chemical Physics Letters 71 (1): 22-26.
  • Irikura K, Goddard III K W A, Beauchamp J L (1992). Singlet-triplet gaps in substituted carbenes CXY (X, Y= H, fluoro, chloro, bromo, iodo, silyl). Journal of the American Chemical Society 114 (1): 48-51.
  • İsmail M A, Batista-Parra A, Miao Y, Wilson W D, Wenzler T, Brun R & Boykin D W (2005). Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents. Bioorganic & medicinal chemistry 13 (24), 6718-6726.
  • Khajehzadeh M & Moghadam M (2018). A new poly (N–heterocyclic carbene Pd complex) immobilized on nano silica: An efficient and reusable catalyst for Suzuki–Miyaura, Sonogashira and Heck–Mizoroki C‒C coupling reactions. Journal of Organometallic Chemistry 863: 60-69.
  • Kühler T C, Swanson M, Christenson B, Klintenberg A C, Lamm B, Fägerhag J & Sjöström J E (2002). Novel Structures Derived from 2-[[(2-Pyridyl) methyl] thio]-1 H-benzimidazole as Anti-Helicobacter p ylori Agents, Part 1. Journal of medicinal chemistry 45 (19): 4282-4299.
  • Lee H M, Chiu P L, Hu C H, Lai C L, Chou Y C (2005). Synthesis and structural characterization of metal complexes based on pyrazole/imidazolium chlorides. Journal of organometallic chemistry 690 (2) 403-414.
  • Mavrava A T, Anchina K K, Vuchev D I, Tesnove J A, Kondeva M S, Miteka K M (2005). Synthesis and antitrichinellosis activity of some 2-substituted-[1,3] thiazolo [3, 2-a] benzimidazol-3(2H)-ones. Bioorganic & medicinal chemistry 13 (19): 5550-5559.
  • Nielsen D J, Cavell K J, Skelton B W & White A H (2003). Tetrafluoroborate anion B-F bond activation-unusual formation of a nucleophilic heterocyclic carbene: BF3 adduct. Inorganica chimica acta 352: 143-150.
  • Nomiya K, Morozumi S, Yanagawa Y, Hasegawa M, Kurose K, Taguchi K & Kasuga N C (2018). Syntheses, structures, and antimicrobial activities of gold (I)–and copper (I)–N-heterocyclic carbene (NHC) complexes derived from basket-shaped dinuclear Ag (I)–NHC complex. Inorganic chemistry 57 (18): 11322-11332.
  • Öfele K. (1968). 1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer Übergangsmetall-carben-komplex. Journal of Organometallic Chemistry, 12 (3): P42-P43.
  • Özdemir İ, Gürbüz N, Doğan Ö, Günal S, Özdemir İ. (2010). Synthesis and antimicrobial activity of Ag (I)‐N‐heterocyclic carbene complexes derived from benzimidazol‐2‐ylidene. Applied Organometallic Chemistry 24 (11): 758-762.
  • Pellei M, Gandin V, Marzano C, Marinelli M, Del Bello F & Santini C (2018). The first water‐soluble copper (I) complexes bearing sulfonated imidazole‐and benzimidazole‐derived N‐heterocyclic carbenes: Synthesis and anticancer studies. Applied Organometallic Chemistry 32 (3): e4185.
  • Pieczykolan M, Czaban-Jóźwiak J, Malinska M, Woźniak K, Dorta R, Rybicka A & Grela K (2020). The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts. Molecules 25 (10): 2282.
  • Pytkowicz J, Roland S, Mangeney P (2001). Synthesis of chiral silver(I) diaminocarbene complexes from (R,R)-4,5-di-tert-butylimidazoline. Journal of Organometallic Chemistry 631 (1-2):157-163.
  • Slimani I, Chakchouk-Mtibaa A, Mellouli L, Mansour L, Ozdemir I, Gürbüz N & Hamdi N (2020). Novel N-Heterocyclic Carbene Silver (I) Complexes: Synthesis, Structural Characterization, Antimicrobial and Cytotoxicity Potential Studies. Journal of the Brazilian Chemical Society 31 (10): 2058-2070.
  • Touj N, Gürbüz N, Hamdi N, Yaşar S & Özdemir İ. (2018). Palladium PEPPSI complexes: Synthesis and catalytic activity on the Suzuki-Miyaura coupling reactions for aryl bromides at room temperature in aqueous media. Inorganica Chimica Acta 478: 187-194.
  • Wanzlick H W & Schönherr H J (1968). Direct synthesis of a mercury salt‐carbene complex. Angewandte Chemie International Edition 7(2): 141-142.
  • Yiğit B, Işık Y, Celepci D B, Evren E, Yiğit M, Gürbüz N, & Özdemir İ. (2020). Ruthenium (II) complexes bearing N-heterocyclic carbene ligands with wingtip groups and their catalytic activity in the transfer hydrogenation of ketones. Inorganica Chimica Acta 499: 119199.
  • Żak P, Bołt M, Kubicki M & Pietraszuk C (2018). Highly selective hydrosilylation of olefins and acetylenes by platinum (0) complexes bearing bulky N-heterocyclic carbene ligands. Dalton Transactions, 47 (6): 1903-1910.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Araştırma Makaleleri
Yazarlar

Ebru ŞAHİN-YILDIRIM Bu kişi benim
CUMHURİYET ÜNİVERSİTESİ, İMRANLI MESLEK YÜKSEKOKULU
0000-0002-4512-8564
Türkiye


Neslihan ŞAHİN> (Sorumlu Yazar)
CUMHURİYET ÜNİVERSİTESİ, EĞİTİM FAKÜLTESİ
0000-0001-5847-6288
Türkiye

Yayımlanma Tarihi 31 Aralık 2020
Yayınlandığı Sayı Yıl 2020, Cilt 10, Sayı 2

Kaynak Göster

APA Şahin-yıldırım, E. & Şahin, N. (2020). Kloro[1-Allil-3-(2-diizopropilaminoetil)benzimidazol-2-iliden]gümüş(I)’in sentezi ve yapısal karakterizasyonu . Ordu Üniversitesi Bilim ve Teknoloji Dergisi , 10 (2) , 66-75 . Retrieved from https://dergipark.org.tr/tr/pub/ordubtd/issue/58759/834959