Synthesis and complexation studies of 16-membered [1+1] selenaaza- and some related macrocycles |
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Authors: | Tapash Chakraborty Snigdha Panda Ray J Butcher |
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Institution: | a Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India b Department of Chemistry, Howard University, Washington, DC 20059, USA |
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Abstract: | A novel 16-membered 1+1] unsymmetrical selenaaza Schiff base macrocycle, 8,9,10,11-tetrahydo-7H-dibenzo-d,o]1,3,7,10,13]diselenatriazacyclohexadecine (5) with N3Se2 donor set, has been synthesized by cyclocondensation of di(o-formylphenylseleno)methane and diethylenetriamine. Reduction of 5 with NaBH4 afforded 6,7,8,9,10,11,12,13-octahydro-5H-dibenzo-d,o]1,3,7,10,13]diselenatriazacyclohexadecine (6). Macrocycle, 10,11,12,13,14,15,16,26,27,28,29,30,31,32-tetradecahydrotetrabenzob,k,n,w]1,13,5,9,17,21]diselenatetraazacyclotetracosine (2b) was synthesized similarly from di(o-formylphenyl)selenide and 1,3-diaminopropane followed by reduction with NaBH4. Single crystal X-ray structures of 5 and 2b have been determined. Attempted complexation reactions of 5 with Zn(II), Cd(II), Hg(II), Pd(II) and Cu(II) ions and those of 6 with Ag(I), Hg(II) and Pd(II) ions are reported. 28-Membered selenaaza macrocycle 2c on reaction with HgCl2 and NH4PF6, provided a dinuclear Hg(II) complex 9. Complex 9 has been characterized by single crystal X-ray structure. |
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Keywords: | Schiff base macrocycle Selenium Mercury [1+1] Cyclocondensation Mercurous ion |
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