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Template Synthesis and Characterization of Transition Metal Complexes of 13, 15 and 17-Membered Tetraamide Macrocyclic Disubstituted Dimethyl Tetrasubstituted Tetraazacycloalka Tetrasubstituted Tetraene Disubstiuted Diol
Corresponding Author(s) : A. Selvan
Asian Journal of Chemistry,
Vol. 32 No. 3 (2020): Vol 32 Issue 3
Abstract
A series of new transition metal complexes [ML(Ln)Cl2] where Ln = L13, L15 and L17 (L(13) = 11,13-dimethyl-1,4,7,10-tetraazacyclotrideca-4,6,10,13-tetraene-5,6-diol, L(15) = 9,11-dimethyl-1,4,8,12-tetraazacyclopentadeca-1,3,8,11-tetraene-2,3-diol and L(17) = 10,12-dimethyl-1,4,9,13-tetraazacycloheptadeca-1,3,9,12-tetraene-2,3-diol) and M = Cu(II), Co(II), Ni(II), Mn(II) and Zn(II) have been synthesized by template method. All the synthesized complexes were characterized by IR, UV, ESR, X-ray microanalysis, elemental analysis, thermal studies and magnetic susceptibilities and the geometry of the complexes found to be octahedral.
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- G.A. Melson, ed., Coordination Chemistry of Macrocyclic Compounds; Plenum: New York (1979).
- R.M. Izatt and J.J. Christensen, eds., Synthesis of Macrocycles: The Design of Selective Complexing Agents, In: Progress in Macrocyclic Chemistry; Wiley-Interscience: New York, vol. 3 (1987).
- R. Chaudhary and R.V. Singh, 28, 35 (2008); https://doi.org/10.1515/REVIC.2008.28.1.35
- N.K. Dalley, In Synthetic Multidentate Macrocyclic Compounds; R.M. Izatt and J. J. Christensen, Eds.; Academic Press: New York, (1978).
- D.A. House and N.F. Curtis, Chem. Ind., 1708 (1961).
- N.F. Curtis, J. Chem. Soc., 4409 (1960); https://doi.org/10.1039/jr9600004409
- N.F. Curtis, Coord. Chem. Rev., 3, 3 (1968); https://doi.org/10.1016/S0010-8545(00)80104-6
- L.F. Lindoy and D.H. Busch, ed.: W.L. Jolly, In Preparative Inorganic Reactions, Wiley-Interscience: New York, vol. 6 (1971).
- M.C. Thompson and D.H. Busch, J. Am. Chem. Soc., 86, 3651 (1964); https://doi.org/10.1021/ja01072a012
- D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17, 69 (1988); https://doi.org/10.1039/cs9881700069
- P. Comba, N.F. Curtis, G.A. Lawrance, A.M. Sargeson, B.W. Skelton and A.H. White, Inorg. Chem., 25, 4260 (1986); https://doi.org/10.1021/ic00243a040
- H. Stetter and W. Frank, Angew. Chem., 88, 760 (1976); https://doi.org/10.1002/ange.19760882208
- H. Hafliger and Th.A. Kaden, Helv. Chim. Acta, 62, 683 (1979); https://doi.org/10.1002/hlca.19790620306
- Th.A. Kaden, eds.: F. Vögtle and E. Weber, Synthesis and Metal Complexes of Aza-Macrocycles with Pendant Arms having Additional Ligating Groups, In: Host Guest Complex Chemistry III, Topics in Current Chemistry, Springer, Berlin, Heidelberg, vol 121, pp. 157-179 (1984).
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- R.M. Izatt, K. Pawlak, J.S. Bradshaw and R.L. Bruening, Chem. Rev., 95, 2529 (1995); https://doi.org/10.1021/cr00039a010
- J.M. Lehn, Supramolecular Chemistry, VCH: New York (1995).
- L.F. Lindoy, Pure Appl. Chem., 69, 2179 (1997); https://doi.org/10.1351/pac199769102179
- P.A. Gale and R. Quesada, Coord. Chem. Rev., 250, 3219 (2006); https://doi.org/10.1016/j.ccr.2006.05.020
- N. Gimeno, R. Vilar, P.A. Gale and R. Quesada, Coord. Chem. Rev., 250, 3161 (2006); https://doi.org/10.1016/j.ccr.2006.05.016
- E. Garcia-Espana, P. Diaz, J.M. Llinares and A. Bianchi, Coord. Chem. Rev., 250, 2952 (2006); https://doi.org/10.1016/j.ccr.2006.05.018
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- K. Bowman-James, Acc. Chem. Res., 38, 671 (2005); https://doi.org/10.1021/ar040071t
- L. Fabbrizzi, M. Licchelli, G. Rabaioli and A. Taglietti, Coord. Chem. Rev., 205, 85 (2000); https://doi.org/10.1016/S0010-8545(00)00239-3
- R. Martinez-Manez and F. Sancenon, Chem. Rev., 103, 4419 (2003); https://doi.org/10.1021/cr010421e
- V. McKee, J. Nelson and R.M. Town, Chem. Soc. Rev., 32, 309 (2003); https://doi.org/10.1039/b200672n
- D.R. Turner, A. Pastor, M. Alajarin and J.W. Steed, Struct. Bonding, 108, 97 (2003); https://doi.org/10.1007/b14138
- M.D. Best, S.L. Tobey and E.V. Anslyn, Coord. Chem. Rev., 240, 3 (2003); https://doi.org/10.1016/S0010-8545(02)00256-4
- P.A. Gale, Coord. Chem. Rev., 240, 191 (2003); https://doi.org/10.1016/S0010-8545(02)00258-8
- J.L. Sessler, S. Camiolo and P.A. Gale, Coord. Chem. Rev., 240, 17 (2003); https://doi.org/10.1016/S0010-8545(03)00023-7
- H.J. Schneider, Angew. Chem., 30, 1417 (1991); https://doi.org/10.1002/anie.199114171
- A.V. Eliseev and H.J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); https://doi.org/10.1021/ja00093a004
- A.C. Warden, M. Warren, M.T.W. Hearn and L. Spiccia, Inorg. Chem., 43, 6936 (2004); https://doi.org/10.1021/ic049633v
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- R. Krämer, Coord. Chem. Rev., 182, 243 (1999); https://doi.org/10.1016/S0010-8545(98)00235-5
- E. Kimura, Curr. Op. Chem. Biol., 4, 207 (2000); https://doi.org/10.1016/S1367-5931(99)00076-9
- S. Aoki and E. Kimura, Rev. Mol. Biotechnol., 90, 129 (2002); https://doi.org/10.1016/S1389-0352(01)00070-8
- L. Fabbrizzi, M. Licchelli and A. Taglietti, Dalton Trans., 3471 (2003); https://doi.org/10.1039/B304172G
- V. Amendola, L. Fabbrizzi, F. Foti, M. Licchelli, C. Mangano, P. Pallavicini, A. Poggi, D. Sacchi and A. Taglietti, Coord. Chem. Rev., 250, 273 (2006); https://doi.org/10.1016/j.ccr.2005.04.022
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- G.A. Melson, Ed. Coordination Chemistry of Macrocyclic Compounds, Plenum: New York (1979).
- L.F. Lindoy, The Chemistry of Macrocyclic Ligand Complexes; Cambridge University Press: Cambridge (1989).
- S. Torelli, C. Belle, I. Gautier-Luneau, J.L. Pierre, E. Saint-Aman, J.M. Latour, L. Le Pape and D. Luneau, Inorg. Chem., 39, 3526 (2000); https://doi.org/10.1021/ic991450z
- O. Kahn, Molecular Magnetism, VCH Publishers Inc.: Weinheim Germany (1993).
- N. Kuhn, Adv. Inorg. Chem., 43, 179 (1995).
- O. Kahn, Acc. Chem. Res., 33, 647 (2000); https://doi.org/10.1021/ar9703138
- C.R. Bondy and S.R. Loeb, Coord. Chem. Rev., 240, 77 (2003); https://doi.org/10.1016/S0010-8545(02)00304-1
- L. Cronin, A.R. Mount, S. Parsons and N. Robertson, J. Chem. Soc., Dalton Trans., 1925 (1999); https://doi.org/10.1039/a902792k
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- A. Bianchi, K. Bowman-James and E. Garcia-Espan, Supramolecular Chemistry of Anions, Wiley-VCH: New York (1997).
- J. Zhao, D. Yang, X.-J. Yang and B. Wu, Coord. Chem. Rev., 378, 415 (2019); https://doi.org/10.1016/j.ccr.2018.01.002
- S. Mason, T. Clifford, L. Seib, K. Kuczera and K. Bowman-James, J. Am. Chem. Soc., 120, 8899 (1998); https://doi.org/10.1021/ja9811593
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- A. Hossain, J.M. Llinares, S. Mason, P. Morehouse, D. Powell and K. Bowman-James, Angew. Chem., Int. Ed., 41, 2335 (2002); https://doi.org/10.1002/1521-3773(20020703)41:13<2335::AIDANIE2335>3.0.CO;2-3
- M.A. Hossain, S.O. Kang, D. Powell and K. Bowman-James, Inorg. Chem., 42, 1397 (2003); https://doi.org/10.1021/ic0263140
- M.A. Hossain, J.M. Llinares, D. Powell and K. Bowman-James, Inorg. Chem., 40, 2936 (2001); https://doi.org/10.1021/ic015508x
References
G.A. Melson, ed., Coordination Chemistry of Macrocyclic Compounds; Plenum: New York (1979).
R.M. Izatt and J.J. Christensen, eds., Synthesis of Macrocycles: The Design of Selective Complexing Agents, In: Progress in Macrocyclic Chemistry; Wiley-Interscience: New York, vol. 3 (1987).
R. Chaudhary and R.V. Singh, 28, 35 (2008); https://doi.org/10.1515/REVIC.2008.28.1.35
N.K. Dalley, In Synthetic Multidentate Macrocyclic Compounds; R.M. Izatt and J. J. Christensen, Eds.; Academic Press: New York, (1978).
D.A. House and N.F. Curtis, Chem. Ind., 1708 (1961).
N.F. Curtis, J. Chem. Soc., 4409 (1960); https://doi.org/10.1039/jr9600004409
N.F. Curtis, Coord. Chem. Rev., 3, 3 (1968); https://doi.org/10.1016/S0010-8545(00)80104-6
L.F. Lindoy and D.H. Busch, ed.: W.L. Jolly, In Preparative Inorganic Reactions, Wiley-Interscience: New York, vol. 6 (1971).
M.C. Thompson and D.H. Busch, J. Am. Chem. Soc., 86, 3651 (1964); https://doi.org/10.1021/ja01072a012
D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17, 69 (1988); https://doi.org/10.1039/cs9881700069
P. Comba, N.F. Curtis, G.A. Lawrance, A.M. Sargeson, B.W. Skelton and A.H. White, Inorg. Chem., 25, 4260 (1986); https://doi.org/10.1021/ic00243a040
H. Stetter and W. Frank, Angew. Chem., 88, 760 (1976); https://doi.org/10.1002/ange.19760882208
H. Hafliger and Th.A. Kaden, Helv. Chim. Acta, 62, 683 (1979); https://doi.org/10.1002/hlca.19790620306
Th.A. Kaden, eds.: F. Vögtle and E. Weber, Synthesis and Metal Complexes of Aza-Macrocycles with Pendant Arms having Additional Ligating Groups, In: Host Guest Complex Chemistry III, Topics in Current Chemistry, Springer, Berlin, Heidelberg, vol 121, pp. 157-179 (1984).
J. Xu, S. Ni and Y. Lin, Inorg. Chim. Acta, 111, 61 (1986); https://doi.org/10.1016/S0020-1693(00)82218-5
R.M. Izatt, K. Pawlak, J.S. Bradshaw and R.L. Bruening, Chem. Rev., 95, 2529 (1995); https://doi.org/10.1021/cr00039a010
J.M. Lehn, Supramolecular Chemistry, VCH: New York (1995).
L.F. Lindoy, Pure Appl. Chem., 69, 2179 (1997); https://doi.org/10.1351/pac199769102179
P.A. Gale and R. Quesada, Coord. Chem. Rev., 250, 3219 (2006); https://doi.org/10.1016/j.ccr.2006.05.020
N. Gimeno, R. Vilar, P.A. Gale and R. Quesada, Coord. Chem. Rev., 250, 3161 (2006); https://doi.org/10.1016/j.ccr.2006.05.016
E. Garcia-Espana, P. Diaz, J.M. Llinares and A. Bianchi, Coord. Chem. Rev., 250, 2952 (2006); https://doi.org/10.1016/j.ccr.2006.05.018
V. Amendola, M. Bonizzoni, D. Esteban-Gomez, L. Fabbrizzi, M. Licchelli, F. Sancenon and A. Taglietti, Coord. Chem. Rev., 250, 1451 (2006); https://doi.org/10.1016/j.ccr.2006.01.006
K. Bowman-James, Acc. Chem. Res., 38, 671 (2005); https://doi.org/10.1021/ar040071t
L. Fabbrizzi, M. Licchelli, G. Rabaioli and A. Taglietti, Coord. Chem. Rev., 205, 85 (2000); https://doi.org/10.1016/S0010-8545(00)00239-3
R. Martinez-Manez and F. Sancenon, Chem. Rev., 103, 4419 (2003); https://doi.org/10.1021/cr010421e
V. McKee, J. Nelson and R.M. Town, Chem. Soc. Rev., 32, 309 (2003); https://doi.org/10.1039/b200672n
D.R. Turner, A. Pastor, M. Alajarin and J.W. Steed, Struct. Bonding, 108, 97 (2003); https://doi.org/10.1007/b14138
M.D. Best, S.L. Tobey and E.V. Anslyn, Coord. Chem. Rev., 240, 3 (2003); https://doi.org/10.1016/S0010-8545(02)00256-4
P.A. Gale, Coord. Chem. Rev., 240, 191 (2003); https://doi.org/10.1016/S0010-8545(02)00258-8
J.L. Sessler, S. Camiolo and P.A. Gale, Coord. Chem. Rev., 240, 17 (2003); https://doi.org/10.1016/S0010-8545(03)00023-7
H.J. Schneider, Angew. Chem., 30, 1417 (1991); https://doi.org/10.1002/anie.199114171
A.V. Eliseev and H.J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); https://doi.org/10.1021/ja00093a004
A.C. Warden, M. Warren, M.T.W. Hearn and L. Spiccia, Inorg. Chem., 43, 6936 (2004); https://doi.org/10.1021/ic049633v
A.C. Warden, M. Warren, M.T.W. Hearn and L. Spiccia, New J. Chem., 28, 1301 (2004); https://doi.org/10.1039/b409088h
L.J.K. Boerner and J.M. Zaleski, Curr. Opin. Chem. Biol., 9, 135 (2005); https://doi.org/10.1016/j.cbpa.2005.02.010
H.-J. Schneider and A. Yatsimirsky, eds.: H. Sigel and A. Sigel, Metal Ion in Biological Systems; Marcel Dekker: New York, vol. 40, pp 369- 462 (2003).
M. Komiyama, eds.: H. Sigel and A. Sigel, Metal Ion in Biological Systems; Marcel Dekker: New York, vol. 40, pp 463-475 (2003).
A. Blasko and T.C. Bruice, Acc. Chem. Res., 32, 475 (1999); https://doi.org/10.1021/ar980060y
E.L. Hegg and J.N. Burstyn, Coord. Chem. Rev., 173, 133 (1998); https://doi.org/10.1016/S0010-8545(98)00157-X
R. Krämer, Coord. Chem. Rev., 182, 243 (1999); https://doi.org/10.1016/S0010-8545(98)00235-5
E. Kimura, Curr. Op. Chem. Biol., 4, 207 (2000); https://doi.org/10.1016/S1367-5931(99)00076-9
S. Aoki and E. Kimura, Rev. Mol. Biotechnol., 90, 129 (2002); https://doi.org/10.1016/S1389-0352(01)00070-8
L. Fabbrizzi, M. Licchelli and A. Taglietti, Dalton Trans., 3471 (2003); https://doi.org/10.1039/B304172G
V. Amendola, L. Fabbrizzi, F. Foti, M. Licchelli, C. Mangano, P. Pallavicini, A. Poggi, D. Sacchi and A. Taglietti, Coord. Chem. Rev., 250, 273 (2006); https://doi.org/10.1016/j.ccr.2005.04.022
A.W. Czarnik and J.-P. Desvergene, Chemosensors of Ions and Molecular Recognition, Kluwer Academic Publishers: Dordrecht, NATO ASI Ser., Ser. C, vol. 492 (1997).
E. Kimura and T. Koike, Chem. Soc. Rev., 27, 179 (1998); https://doi.org/10.1039/a827179z
G.A. Melson, Ed. Coordination Chemistry of Macrocyclic Compounds, Plenum: New York (1979).
L.F. Lindoy, The Chemistry of Macrocyclic Ligand Complexes; Cambridge University Press: Cambridge (1989).
S. Torelli, C. Belle, I. Gautier-Luneau, J.L. Pierre, E. Saint-Aman, J.M. Latour, L. Le Pape and D. Luneau, Inorg. Chem., 39, 3526 (2000); https://doi.org/10.1021/ic991450z
O. Kahn, Molecular Magnetism, VCH Publishers Inc.: Weinheim Germany (1993).
N. Kuhn, Adv. Inorg. Chem., 43, 179 (1995).
O. Kahn, Acc. Chem. Res., 33, 647 (2000); https://doi.org/10.1021/ar9703138
C.R. Bondy and S.R. Loeb, Coord. Chem. Rev., 240, 77 (2003); https://doi.org/10.1016/S0010-8545(02)00304-1
L. Cronin, A.R. Mount, S. Parsons and N. Robertson, J. Chem. Soc., Dalton Trans., 1925 (1999); https://doi.org/10.1039/a902792k
H.-Z. Kou, B.C. Zhou, S. Gao and R.-J. Wang, Angew. Chem. Int. Ed., 42, 3288 (2003); https://doi.org/10.1002/anie.200351248
J.-K. Tang, S.-F. Si, L.-Y. Wang, D.-Z. Liao, Z.-H. Jiang, S.P. Yan, P. Cheng and X. Liu, Inorg. Chim. Acta, 343, 288 (2003); https://doi.org/10.1016/S0020-1693(02)01241-0
A. Bianchi, K. Bowman-James and E. Garcia-Espan, Supramolecular Chemistry of Anions, Wiley-VCH: New York (1997).
J. Zhao, D. Yang, X.-J. Yang and B. Wu, Coord. Chem. Rev., 378, 415 (2019); https://doi.org/10.1016/j.ccr.2018.01.002
S. Mason, T. Clifford, L. Seib, K. Kuczera and K. Bowman-James, J. Am. Chem. Soc., 120, 8899 (1998); https://doi.org/10.1021/ja9811593
T. Clifford, A. Danby, J.M. Llinares, S. Mason, N.W. Alcock, D. Powell, J.A. Aguilar, E. Garcia-Espan and K. Bowman-James, Inorg. Chem., 40, 4710 (2001); https://doi.org/10.1021/ic010135l
A. Hossain, J.M. Llinares, S. Mason, P. Morehouse, D. Powell and K. Bowman-James, Angew. Chem., Int. Ed., 41, 2335 (2002); https://doi.org/10.1002/1521-3773(20020703)41:13<2335::AIDANIE2335>3.0.CO;2-3
M.A. Hossain, S.O. Kang, D. Powell and K. Bowman-James, Inorg. Chem., 42, 1397 (2003); https://doi.org/10.1021/ic0263140
M.A. Hossain, J.M. Llinares, D. Powell and K. Bowman-James, Inorg. Chem., 40, 2936 (2001); https://doi.org/10.1021/ic015508x