Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Organotellurium Compounds: From Molecular to Supramolecular Chemistry: A Review
Corresponding Author(s) : S. Bajpai
Asian Journal of Chemistry,
Vol. 30 No. 6 (2018): Vol 30 Issue 6
Abstract
Supramolecules wherein discrete molecules are held together by non-covalent interactions are well known. It is more frequent in compounds containing conformational flexible molecule and functional groups like -COOH, -OH, -NH2 that can participate in weak secondary interaction, thereby dictating the self-assembly. Moreover, metal complexes with different coordinating ligands can participate in supramolecular aggregations. Organotellurium compounds due to their unique property of hypervalency, three centre bonding and secondary bonding interactions finds its way towards supramolecular chemistry. The journey of organotellurium compounds from molecular to supramolecular chemistry is depicted here with reference to some selected examples.
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- N. Petragnani and L. Wai-Ling, J. Braz. Chem. Soc., 9, 415 (1998); https://doi.org/10.1590/S0103-50531998000500002.
- F. Wöhler, Ann. Chem, 35, 111 (1840); https://doi.org/10.1002/jlac.18400350108.
- K. Lederer, Chem. Ber., 44, 2287 (1911); https://doi.org/10.1002/cber.19110440344.
- W. Cooper, Tellurium, Van Nostrand, New York (1977).
- K.J. Irgolic, The Organic Chemistry of Tellurium, Gordon and Breach, New York (1974).
- K.J. Irgolic, J. Organomet. Chem., 103, 91 (1975); https://doi.org/10.1016/S0022-328X(00)89237-2.
- K.J. Irgolic, J. Organomet. Chem., 130, 411 (1977); https://doi.org/10.1016/S0022-328X(00)92264-2.
- K.J. Irgolic, J. Organomet. Chem., 158, 235 (1978); https://doi.org/10.1016/S0022-328X(00)89679-5.
- K.J. Irgolic, J. Organomet. Chem., 158, 267 (1978); https://doi.org/10.1016/S0022-328X(00)89680-1.
- K.J. Irgolic, J. Organomet. Chem., 189, 65 (1980); https://doi.org/10.1016/S0022-328X(00)85940-9.
- K.J. Irgolic, J. Organomet. Chem., 203, 376 (1980); https://doi.org/10.1016/S0022-328X(00)83957-1.
- G. Pattenden, Saturated Heterocyclic Chemistry, The Royal Society of Chemistry, London (1973-1978).
- C. Bird and G. Cheeseman, Aromatic and Heteroaromatic Chemistry, The Royal Society of Chemistry, London, vols. 1-5 (1973-1977).
- H. Suschitzky and O. Meth-Cohn, Aromatic and Heteroaromatic Chemistry, The Royal Society of Chemistry, London, vols. 6-7 (1978-1979).
- D. Reid, Organic Compounds of Sulfur, Selenium and Tellurium, The Royal Society of Chemistry, London, vols. 1-6 (1970-1981).
- H. Suschitzky and O. Meth-Cohn, Heterocyclic Chemistry, The Royal Society of Chemistry, London (1980).
- L. Christiaens, eds.: D. Cagniant and G. Kirsch, Proceedings of the Third International Symposium on Organic Se and Te Compounds, University of Metz, p. 69 (1979).
- S. Patai and Z. Rappoport, The Chemistry of Organic Selenium and Tellurium Compounds, John Wiley & Sons, N.Y., USA, vols. 1 & 2 (1986).
- I.D. Sadekov and V.I. Minkin, Usp. Khim., 64, 491 (1995); https://doi.org/10.1070/RC1995v064n06ABEH000162.
- I. Haiduc and F.T. Edelmann, Supramolecular Organometallic Chemistry, Wiley VCH, Weinheim, New York (1999).
- I. Haiduc, R.B. King and M.G. Newton, Chem. Rev., 94, 301 (1994); https://doi.org/10.1021/cr00026a002.
- I. Haiduc and J. Zukerman-Schpector, Phosphorus Sulfur Silicon Rel. Elem., 171, 171 (2001); https://doi.org/10.1080/10426500108046632.
- J.H.E. Bailey, J.E. Drake and M.L.Y. Wong, Can. J. Chem., 69, 1948 (1991); https://doi.org/10.1139/v91-280.
- J.H.E. Bailey and J.E. Drake, Can. J. Chem., 71, 42 (1993); https://doi.org/10.1139/v93-007.
- J.E. Drake, R.J. Drake, L.N. Khasrou and R. Ratnani, Inorg. Chem., 35, 2831 (1996); https://doi.org/10.1021/ic9511736.
- J.E. Drake, L.N. Khasrou, A.G. Mislankar and R. Ratnani, Inorg. Chem., 38, 3994 (1999); https://doi.org/10.1021/ic990281f.
- J.E. Drake and J. Yang, Inorg. Chem., 36, 1890 (1997); https://doi.org/10.1021/ic9608455.
- D. Dakternieks, R.D. Giacomo, R.W. Gable and B.F. Hoskins, J. Am. Chem. Soc., 110, 6753 (1988); https://doi.org/10.1021/ja00228a025.
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- J.O. Bogason, D. Dakternieks, S. Husebye, K. Maartmann-Moe and H. Zhu, Phosphorus Sulfur Silicon Rel. Elem., 71, 13 (1992); https://doi.org/10.1080/10426509208034492.
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- P.C. Srivastava, S. Dwivedi, V. Singh and R.J. Butcher, Polyhedron, 29, 2202 (2010); https://doi.org/10.1016/j.poly.2010.04.020.
- K. Kandasamy, S. Kumar, H.B. Singh and G. Wolmershäuser, Organometallics, 22, 5069 (2003); https://doi.org/10.1021/om0340948.
- A.M. Cotero-Villegas, P.G. García, H. Hopfl, M. del Carman Perez-Redondo, P. Martinez-Salas, M. Lopez-Cardoso and R.C. Olivares, J. Organomet. Chem., 695, 1246 (2010); https://doi.org/10.1016/j.jorganchem.2010.01.036.
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- P.C. Srivastava, V. Singh, S. Dwivedi and R.J. Butcher, Indian J. Chem., 49A, 1197 (2010).
- P.C. Srivastava, S. Bajpai, S. Bajpai, R. Kumar, S. Srivastava and R.J. Butcher, Struct. Chem., 18, 223 (2007); https://doi.org/10.1007/s11224-006-9092-3.
- A.K.S. Chauhan, A. Kumar, R.C. Srivastava and R.J. Butcher, J. Organomet. Chem., 658, 169 (2002); https://doi.org/10.1016/S0022-328X(02)01648-0.
- D. Braga, F. Grepioni, K. Biradha, V.R. Pedireddi and G.R. Desiraju, J. Am. Chem. Soc., 117, 3156 (1995); https://doi.org/10.1021/ja00116a020.
- G.R. Desiraju, Acc. Chem. Res., 29, 441 (1996); https://doi.org/10.1021/ar950135n.
- P.C. Srivastava, S. Bajpai, R. Lath, C. Ram, S. Bajpai, R.J. Butcher, M. Zimmer and M. Veith, J. Organomet. Chem., 649, 70 (2002); https://doi.org/10.1016/S0022-328X(02)01124-5.
- A.K.S. Chauhan, A. Kumar, R.C. Srivastava, J. Beckmann, A. Duthie and R.J. Butcher, J. Organomet. Chem., 689, 345 (2004); https://doi.org/10.1016/j.jorganchem.2003.10.021.
- A.K.S. Chauhan, P. Singh, R.C. Srivastava, A. Duthie and A. Voda, Dalton Trans., 4023 (2008); https://doi.org/10.1039/b800473k.
- B. Kersting, Z. Naturforsch., 57, 1115 (2002).
- P. C. Srivastava, S. Bajpai, C. Ram, R. Kumar, S. Srivastava and R.J. Butcher, Proc. Nat. Acad. Sci. India, 76, 109 (2006).
- P.C. Srivastava, S. Bajpai, C. Ram, R. Kumar and R.J. Butcher, J. Organomet. Chem., 692, 2482 (2007); https://doi.org/10.1016/j.jorganchem.2007.02.026.
- V. Chandrasekhar and A. Kumar, J. Organomet. Chem., 694, 2628 (2009); https://doi.org/10.1016/j.jorganchem.2009.03.042.
- P.C. Srivastava, S. Dwivedi, V. Singh, T. Pujan, A.K. Bhuj, R.J. Butcher, M.B.M. Krishna and D.N. Rao, Inorg. Chim. Acta, 388, 175 (2012); https://doi.org/10.1016/j.ica.2012.02.047.
- P.C. Srivastava, V. Singh, S. Dwivedi, T. Pujan, A.K. Bhuj, R.J. Butcher, M.B. Murali Krishna and D.N. Rao, Polyhedron, 42, 36 (2012); https://doi.org/10.1016/j.poly.2012.04.035.
- T. Pujan, Ph.D. Thesis, Synthesis, Reactions, Characterization and Supramolecular Associations of Some Organotellurium Derivatives, Shodganga@INFLIBNET (2015).
References
N. Petragnani and L. Wai-Ling, J. Braz. Chem. Soc., 9, 415 (1998); https://doi.org/10.1590/S0103-50531998000500002.
F. Wöhler, Ann. Chem, 35, 111 (1840); https://doi.org/10.1002/jlac.18400350108.
K. Lederer, Chem. Ber., 44, 2287 (1911); https://doi.org/10.1002/cber.19110440344.
W. Cooper, Tellurium, Van Nostrand, New York (1977).
K.J. Irgolic, The Organic Chemistry of Tellurium, Gordon and Breach, New York (1974).
K.J. Irgolic, J. Organomet. Chem., 103, 91 (1975); https://doi.org/10.1016/S0022-328X(00)89237-2.
K.J. Irgolic, J. Organomet. Chem., 130, 411 (1977); https://doi.org/10.1016/S0022-328X(00)92264-2.
K.J. Irgolic, J. Organomet. Chem., 158, 235 (1978); https://doi.org/10.1016/S0022-328X(00)89679-5.
K.J. Irgolic, J. Organomet. Chem., 158, 267 (1978); https://doi.org/10.1016/S0022-328X(00)89680-1.
K.J. Irgolic, J. Organomet. Chem., 189, 65 (1980); https://doi.org/10.1016/S0022-328X(00)85940-9.
K.J. Irgolic, J. Organomet. Chem., 203, 376 (1980); https://doi.org/10.1016/S0022-328X(00)83957-1.
G. Pattenden, Saturated Heterocyclic Chemistry, The Royal Society of Chemistry, London (1973-1978).
C. Bird and G. Cheeseman, Aromatic and Heteroaromatic Chemistry, The Royal Society of Chemistry, London, vols. 1-5 (1973-1977).
H. Suschitzky and O. Meth-Cohn, Aromatic and Heteroaromatic Chemistry, The Royal Society of Chemistry, London, vols. 6-7 (1978-1979).
D. Reid, Organic Compounds of Sulfur, Selenium and Tellurium, The Royal Society of Chemistry, London, vols. 1-6 (1970-1981).
H. Suschitzky and O. Meth-Cohn, Heterocyclic Chemistry, The Royal Society of Chemistry, London (1980).
L. Christiaens, eds.: D. Cagniant and G. Kirsch, Proceedings of the Third International Symposium on Organic Se and Te Compounds, University of Metz, p. 69 (1979).
S. Patai and Z. Rappoport, The Chemistry of Organic Selenium and Tellurium Compounds, John Wiley & Sons, N.Y., USA, vols. 1 & 2 (1986).
I.D. Sadekov and V.I. Minkin, Usp. Khim., 64, 491 (1995); https://doi.org/10.1070/RC1995v064n06ABEH000162.
I. Haiduc and F.T. Edelmann, Supramolecular Organometallic Chemistry, Wiley VCH, Weinheim, New York (1999).
I. Haiduc, R.B. King and M.G. Newton, Chem. Rev., 94, 301 (1994); https://doi.org/10.1021/cr00026a002.
I. Haiduc and J. Zukerman-Schpector, Phosphorus Sulfur Silicon Rel. Elem., 171, 171 (2001); https://doi.org/10.1080/10426500108046632.
J.H.E. Bailey, J.E. Drake and M.L.Y. Wong, Can. J. Chem., 69, 1948 (1991); https://doi.org/10.1139/v91-280.
J.H.E. Bailey and J.E. Drake, Can. J. Chem., 71, 42 (1993); https://doi.org/10.1139/v93-007.
J.E. Drake, R.J. Drake, L.N. Khasrou and R. Ratnani, Inorg. Chem., 35, 2831 (1996); https://doi.org/10.1021/ic9511736.
J.E. Drake, L.N. Khasrou, A.G. Mislankar and R. Ratnani, Inorg. Chem., 38, 3994 (1999); https://doi.org/10.1021/ic990281f.
J.E. Drake and J. Yang, Inorg. Chem., 36, 1890 (1997); https://doi.org/10.1021/ic9608455.
D. Dakternieks, R.D. Giacomo, R.W. Gable and B.F. Hoskins, J. Am. Chem. Soc., 110, 6753 (1988); https://doi.org/10.1021/ja00228a025.
D. Dakternieks, R. DiGiacomo, R.W. Gable and B.F. Hoskins, J. Organomet. Chem., 353, 35 (1988); https://doi.org/10.1016/0022-328X(88)80297-3.
J.O. Bogason, D. Dakternieks, S. Husebye, K. Maartmann-Moe and H. Zhu, Phosphorus Sulfur Silicon Rel. Elem., 71, 13 (1992); https://doi.org/10.1080/10426509208034492.
V. García-Montalvo, A. Marcelo-Polo, R. Montoya, R.A. Toscano, S. Hernández-Ortega and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); https://doi.org/10.1016/S0022-328X(00)00718-X.
S. Husebye, K. Maartmann-Moe, W. Steffensen, D.T. Beattie, P. KrogsgaardLarsen, K. Maartmann-Moe and S. Wold, Acta Chem. Scand., 44, 139 (1990); https://doi.org/10.3891/acta.chem.scand.44-0139.
P.C. Srivastava, S. Dwivedi, V. Singh and R.J. Butcher, Polyhedron, 29, 2202 (2010); https://doi.org/10.1016/j.poly.2010.04.020.
K. Kandasamy, S. Kumar, H.B. Singh and G. Wolmershäuser, Organometallics, 22, 5069 (2003); https://doi.org/10.1021/om0340948.
A.M. Cotero-Villegas, P.G. García, H. Hopfl, M. del Carman Perez-Redondo, P. Martinez-Salas, M. Lopez-Cardoso and R.C. Olivares, J. Organomet. Chem., 695, 1246 (2010); https://doi.org/10.1016/j.jorganchem.2010.01.036.
A.M. Cotero-Villegas, P.G. García, H. Hopfl, M. del Carman Perez-Redondo, P. Martinez-Salas, M. Lopez-Cardoso and R.C. Olivares, J. Organomet. Chem., 696, 2071 (2011); https://doi.org/10.1016/j.jorganchem.2010.11.006.
P.C. Srivastava, S. Bajpai, R. Lath and R.J. Butcher, J. Organomet. Chem., 608, 96 (2000); https://doi.org/10.1016/S0022-328X(00)00379-X.
P.C. Srivastava, S. Bajpai, S. Bajpai, C. Ram, R. Kumar, J.P. Jasinski and R.J. Butcher, J. Organomet. Chem., 689, 194 (2004); https://doi.org/10.1016/j.jorganchem.2003.10.003.
P.C. Srivastava, Sm. Bajpai, S. Bajpai, R. Kumar and R.J. Butcher, Indian J. Chem., 43A, 2558 (2004).
P.C. Srivastava, S. Bajpai, R. Lath, S.M. Bajpai, R. Kumar and R.J. Butcher, Polyhedron, 23, 1629 (2004); https://doi.org/10.1016/j.poly.2004.03.019.
J. Beckmann, D. Dakternieks, A. Duthie and N.A. Smith, J. Organomet. Chem., 669, 149 (2003); https://doi.org/10.1016/S0022-328X(03)00005-6.
J. Zukerman-Schpector, I. Haiduc, R.L. Camillo, J.V. Comasseto, R.L.O.R. Cunha and A. Jorge, Can. J. Chem., 80, 1530 (2002); https://doi.org/10.1139/v02-136.
E.S. Lang, R.M. Fernandes Jr., C. Peppe, R.A. Burrow and E.M. VázquezLópez, Z. Anorg. Allg. Chem., 629, 215 (2003); https://doi.org/10.1002/zaac.200390034.
P.C. Srivastava, V. Singh, S. Dwivedi and R.J. Butcher, Indian J. Chem., 49A, 1197 (2010).
P.C. Srivastava, S. Bajpai, S. Bajpai, R. Kumar, S. Srivastava and R.J. Butcher, Struct. Chem., 18, 223 (2007); https://doi.org/10.1007/s11224-006-9092-3.
A.K.S. Chauhan, A. Kumar, R.C. Srivastava and R.J. Butcher, J. Organomet. Chem., 658, 169 (2002); https://doi.org/10.1016/S0022-328X(02)01648-0.
D. Braga, F. Grepioni, K. Biradha, V.R. Pedireddi and G.R. Desiraju, J. Am. Chem. Soc., 117, 3156 (1995); https://doi.org/10.1021/ja00116a020.
G.R. Desiraju, Acc. Chem. Res., 29, 441 (1996); https://doi.org/10.1021/ar950135n.
P.C. Srivastava, S. Bajpai, R. Lath, C. Ram, S. Bajpai, R.J. Butcher, M. Zimmer and M. Veith, J. Organomet. Chem., 649, 70 (2002); https://doi.org/10.1016/S0022-328X(02)01124-5.
A.K.S. Chauhan, A. Kumar, R.C. Srivastava, J. Beckmann, A. Duthie and R.J. Butcher, J. Organomet. Chem., 689, 345 (2004); https://doi.org/10.1016/j.jorganchem.2003.10.021.
A.K.S. Chauhan, P. Singh, R.C. Srivastava, A. Duthie and A. Voda, Dalton Trans., 4023 (2008); https://doi.org/10.1039/b800473k.
B. Kersting, Z. Naturforsch., 57, 1115 (2002).
P. C. Srivastava, S. Bajpai, C. Ram, R. Kumar, S. Srivastava and R.J. Butcher, Proc. Nat. Acad. Sci. India, 76, 109 (2006).
P.C. Srivastava, S. Bajpai, C. Ram, R. Kumar and R.J. Butcher, J. Organomet. Chem., 692, 2482 (2007); https://doi.org/10.1016/j.jorganchem.2007.02.026.
V. Chandrasekhar and A. Kumar, J. Organomet. Chem., 694, 2628 (2009); https://doi.org/10.1016/j.jorganchem.2009.03.042.
P.C. Srivastava, S. Dwivedi, V. Singh, T. Pujan, A.K. Bhuj, R.J. Butcher, M.B.M. Krishna and D.N. Rao, Inorg. Chim. Acta, 388, 175 (2012); https://doi.org/10.1016/j.ica.2012.02.047.
P.C. Srivastava, V. Singh, S. Dwivedi, T. Pujan, A.K. Bhuj, R.J. Butcher, M.B. Murali Krishna and D.N. Rao, Polyhedron, 42, 36 (2012); https://doi.org/10.1016/j.poly.2012.04.035.
T. Pujan, Ph.D. Thesis, Synthesis, Reactions, Characterization and Supramolecular Associations of Some Organotellurium Derivatives, Shodganga@INFLIBNET (2015).