Synthesis and complexation studies of 16-membered [1+1] selenaaza- and some related macrocycles

Tapash Chakraborty, Kriti Srivastava, Snigdha Panda, Harkesh B. Singh, Ray J. Butcher

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10 Scopus citations


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-tetradecahydrotetrabenzo[b,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.

Original languageEnglish (US)
Pages (from-to)2905-2911
Number of pages7
JournalInorganica Chimica Acta
Issue number12
StatePublished - Oct 15 2010

Bibliographical note

Funding Information:
We are thankful to the MHz NMR spectroscopy is gratefully acknowledged. We gratefully acknowledge Dr. A. Panda for help in the synthesis of the macrocyclic ligand Department of Science and Technology (DST), India for funding this work. Additional help from the Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology, Bombay, for 300 2b . T.C. and K.S. are also grateful to the Council of Scientific and Industrial Research, India for providing fellowship.


  • Mercurous ion
  • Mercury
  • Schiff base macrocycle
  • Selenium


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