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

doi:10.1016/j.ica.2010.03.020

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

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-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 language	English (US)
Pages (from-to)	2905-2911
Number of pages	7
Journal	Inorganica Chimica Acta
Volume	363
Issue number	12
DOIs	https://doi.org/10.1016/j.ica.2010.03.020
State	Published - 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.

Keywords

Mercurous ion
Mercury
Schiff base macrocycle
Selenium

Access

10.1016/j.ica.2010.03.020

OpenUrl availability

Full text

Cite this

@article{085e6d684f2e4f6dbae416789e21fda8,

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

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-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.",

keywords = "Mercurous ion, Mercury, Schiff base macrocycle, Selenium",

author = "Tapash Chakraborty and Kriti Srivastava and Snigdha Panda and Singh, {Harkesh B.} and Butcher, {Ray J.}",

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.",

year = "2010",

month = oct,

day = "15",

doi = "10.1016/j.ica.2010.03.020",

language = "English (US)",

volume = "363",

pages = "2905--2911",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

publisher = "Elsevier BV",

number = "12",

}

TY - JOUR

T1 - Synthesis and complexation studies of 16-membered [1+1] selenaaza- and some related macrocycles

AU - Chakraborty, Tapash

AU - Srivastava, Kriti

AU - Panda, Snigdha

AU - Singh, Harkesh B.

AU - Butcher, Ray J.

N1 - 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.

PY - 2010/10/15

Y1 - 2010/10/15

N2 - 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.

AB - 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.

KW - Mercurous ion

KW - Mercury

KW - Schiff base macrocycle

KW - Selenium

UR - http://www.scopus.com/inward/record.url?scp=77957313939&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77957313939&partnerID=8YFLogxK

U2 - 10.1016/j.ica.2010.03.020

DO - 10.1016/j.ica.2010.03.020

M3 - Article

AN - SCOPUS:77957313939

SN - 0020-1693

VL - 363

SP - 2905

EP - 2911

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

IS - 12

ER -

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

Abstract

Bibliographical note

Keywords

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this