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THE SYNTHESIS AND THE STRUCTURAL INVESTIGATIONS OF CRYPTAND [3.2.1] AND N,N′-BISFORMYL [3.2] LARIAT ETHER LIGANDS

Year 2006, Issue: 010, 33 - 44, 15.05.2006

S. Bilge Z. Kılıç

Abstract

From the reaction of dibenzo-diaza-crown ethers, which are 17- and 18-membered rings composed of N2O3-donor type, with paraformaldehyde in benzene, the first examples of cryptand [3.2.1] type ligands have been obtained. The reaction of cryptand (2) with Pd(CH3COO)2 (mediator) in the mixture of CH2Cl2/C6H6 (1/1) led to the formation of N,N′-bisformyl [3.2] (BiBLE) lariat ether (3). The structures of cryptand and BiBLE lariat ethers have been characterized by elemental analyses, MS, FT-IR, 1H-, 13C-NMR and HETCOR spectral data. The spectral data of the compounds have also been compared with the available data of related dibenzo-diaza-crown ethers.

Keywords

Dibenzo-diaza-crown ethers BiBLE lariat ethers Cryptands

References

  • [1] Vögtle, F. and Weber, E., ‘‘Host guest complex chemistry III’’, Topics in Current in Chemistry, (Ed: Weber, E.), Springer, New York, 1-187 (1984).
  • [2] Winefordner, J.D., ‘‘Macrocyclic compounds in analytical chemistry’’, Chemical Analysis, Vol.143, John Wiley and Sons, New York, 1-424 (1997).
  • [3] Lindoy, L., ‘‘Heavy metal chemistry of mixed donor macrocyclic ligands: Strategies for obtaining metal ion recognition’’, Progress in Macrocyclic Chemistry, Vol. 3, John Wiley and Sons, New York, 53-97 (1987).
  • [4] Weber, E. and Vögtle, F., ‘‘Classification and nomenclature of coronands, cryptands, podands, and of their complexes’’, Inorg. Chim. Acta, 45: 65-67 (1980).
  • [5] Gokel, G.W., ‘‘Crown ethers and cryptands’’, Monographs in Supramolecular Chemistry, Coral Gables, Florida, U.S.A., 1-63 (1991).
  • [6] Goodwin, H.J., Henrick, K., Lindoy, L.F., McPartlin, M. and Tasker, P.A., ‘‘Studies of macrocylic ligand hole sizes. 1. X-ray structures of the nickel bromide complexes of the diimine and reduced forms of a 16-membered macrocyclic ring incorporating O2N2 donors’’, Inorg. Chem., 21: 3261-3264 (1982).
  • [7] Bilge, S., Kılıç, Z., Hökelek, T. and Erdoğan, B., ‘‘Complexes of Ni (II) and Pd (II) ions with 15- and 17-membered macrocycles containing O2N2- and O2N3-donors and the crystal structures of Ni(II) and Pd(II) complexes of 2,5-dioxa-13,16,19- triazatricyclo[19.4.0.06,11]-pentacosa-6,8,10,21,23,25(1)-hexaene’’, J. Mol. Struct., 691: 85-96 (2004).
  • [8] Adam, K.R., Clarkson, C., Leong A.J., Lindoy, L.F., McPartlin, M., Powell, H.R. and Smith, S.V., ‘‘Interaction of transition and post-transsition metal ions with oxygennitrogen donor macrocycles incorporating pendant hydroxyethyl and carbamoylethyl groups’’, J. Chem. Soc., Dalton Trans., 2791-2798 (1994).
  • [9] Hökelek, T., Kılıç, Z. and Bilge, S., ‘‘5,6,7,8,9,10,11,12,18,19,21,22-Dodecahydro- 8,9:18,19-dibenzo-1,4,7-trioxa-11,16-diazacyclononadeca-10,16-diene’’, Acta Cryst., C55: 381-383 (1999).
  • [10] Hökelek, T., Bilge, S., Akduran, N. and Kılıç, Z., ‘‘Crystal structure of 15,21- bis(diethoxyphosphinoyl)-2,5,8-trioxa-16,20-diazatricyclo [20.4.0.09,14] hexacosa-9,11,13,22,24,26(1)-hexaene-ethylphosphonic acid-water (1/1/1)’’, Cryst. Res. Technol., 36: 509-515 (2001).
  • [11] Bilge, S., Natsagdorj, A., Akduran, N., Hökelek, T. and Kılıç, Z., ‘‘C-bis-pivot podands and lariat ethers: Synthesis and spectral investigations. Structure of 15,21- bis{2-[(hydroxy)(methoxy)phosphoryl]}-2,5,8-trioxa-16,20-diazatricyclo[20.4.0.09,14] hexacosa-9,11,13,22,24,26(1)-hexaene-water (1/2)’’, J. Mol. Struct., 611: 169-178 (2002).
  • [12] Hökelek, T., Akduran, N., Bilge, S. and Kılıç, Z., ‘‘Crystal structure of 2,5-dioxa- 13,17-diazatricyclo[17.4.0.06,11]tricosa-6,8,10,12,17,19,21,23(1)-octaene’’, Anal. Sci., 18: 1065-1066 (2002).
  • [13] Hökelek, T., Bilge, S. and Kılıç, Z., ‘‘1,15-Diaza-3,4:12,13-dibenzo-5,8,11- trioxacycloheptadecane hemihydrate’’, Acta Cryst., E59: 1607-1609 (2003).
  • [14] Hökelek, T., Akduran, N., Bilge, S. and Kılıç, Z., ‘‘Crystal structure of3,4,6,7,15,16,17,18,19,20,21-undecahydro-2,5,6-trioxa-16,20-diazatricyclo [20.4.0.09,14]hexacosa-9,11,13,22,24,26(1)-hexaene’’, Anal. Sci., 17: 801-802 (2001).
  • [15] Hökelek, T., Akduran, N., Bilge, S. and Kılıç, Z., ‘‘Crystal structure of 3,4,6,7,15,16,17,18,19,20,21,27-dodecahydro-2,5,8-trioxa-16,20-diazatetracyclo [20.4.116,20.0.09,14]heptacosa-9,11,13,22,24,26(1)-hexaene’’, Anal. Sci., 17: 465-466 (2001).
  • [16] Adam, K.R., Leong, A.J., Lindoy, L.F., Lip, H.C., Skelton, B.W. and White, A.H., ‘‘Ligand design and metal-ion recognition. interaction of Ni(II) with 17- to 19- membered macrocycles containing O2N3 and O3N2 donor sets and the X-ray structure of the parent 17-membered macrocyclic ligand’’, J. Am. Chem. Soc., 105: 4645-4651 (1983).
  • [17] Hökelek, T., Kılıç, Z. and Bilge, S., ‘‘2,5,8-Trioxa-16,20-diazatricyclo [20.4.0.09,14]hexacosa-9,11,13,15,20,22,24,26-octaene’’, Acta Cryst., C55: 248-250 (1999).
  • [18] Zhang, J., Vittal, J., Henderson, W., Wheaton, J.R., Hall, I.H., Hor, T.S.A. and Yan, Y.K., ‘‘Tricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: Structures, solution behavior and cytotoxicity’’, J. Org. Chem., 650: 123-132 (2002).
  • [19] Hökelek, T., Yamak, İ. and Kılıç, Z., ‘‘Crystal structure of N,N,N′,N′- tetrakis(methyldiphenylphosphino)-bis(2′-phenoxy)-3,6 dioxaoctane’’, Anal. Sci., 19: 465-466 (2003).
  • [20] Dutasta, J.P., Declercq, J.P., Calderon, C.E. and Tinant, B., ‘‘Novel ditopic receptors based on the P2N2 diphosphazene ring; synthesis and X-ray structural characterizationof cis and trans bis(crown ether) annellated 1,3,2λ5,4λ5-diazadiphosphetidine-2,4 disulfide’’, J. Am. Chem. Soc., 111: 7136-7144 (1989).
  • [21] Yamak, İ., Lariat taç (crown) eterlerin ve komplekslerinin sentezi, yapılarının spektroskopik ve kristallografik yöntemler ile qydınlatılması, Doktora Tezi, Ankara Ünv. Fen Bilm. Ens., No.257 (2001).
  • [22] Kyba, E.P., Davis, R.E ., Hudson, C.W., John, A.M., Brown, S.B., McPaul, M.J., Liu, L. and Glover, C., ‘‘Tetradentate 14-membered tert-phosphino-containing macrocycles’’, J. Am. Chem. Soc., 103: 3868-3875 (1981).
  • [23] McLain, S.J., ‘‘Organometallic crown ethers. 1. Metal acyl binding to a crown ether held cation’’, J. Am. Chem. Soc., 105: 6355-6357 (1983).
  • [24] Power, P.P., Hope, H., Viggiano, M. and Moezzi, B., ‘‘Syntheses and X-ray crystal structures of two new classes of macrocyclic ligands having both phosphorus and nitrogen donor atoms’’, Inorg. Chem., 23: 2550-2552 (1984).
  • [25] Balch, A.L. and Rowley, S.P., ‘‘Sobulizing the thallium-platinum unit of Tl2Pt(CN)4. Preparation and use of a new crown ether / phoshine hybrid ligand for linking maingroup and transition-metal ions’’, J. Am. Chem. Soc., 112: 6139-6140 (1990).
  • [26] Lindoy, L.F., Skelton, B.W., Smith, S.V. and White, A.H., ‘‘New macrocyclic ligands. III. Pendant 2-pyridylmethyl of dibenzo-substituted O2N2-donor rings. The X-ray structure of a pendant 2-pyridylmethyl derivative’’, Aust. J. Chem., 46: 363-375 (1993).
  • [27] Bilge, S., Kılıç, Z., Çaylak, N. and Hökelek, T., ‘‘Phosphorus-nitrogen compounds: Novel spiro-crypta-phosphazenes. Structure of {pentane-3-oxa-N,N’-bis(1,5-oxybenzyl)-spiro(etane-1′,2′-diamino)-4,4,6,6-tetrachlorocyclo-2λ5,4λ5,6λ5- triphosphazatriene}. Part IX’’, J. Mol. Struct., 707: 139-146 (2004).

KRİPTAND [3.2.1] VE N,N′-BİSFORMİL [3.2] LARİAT ETER LİGANDLARININ SENTEZİ VE YAPILARININ İNCELENMESİ

Year 2006, Issue: 010, 33 - 44, 15.05.2006

S. Bilge Z. Kılıç

Abstract

N2O3-Donor atomlarından meydana gelen 17- ve 18-üyeli dibenzo-diaza-taç eterlerin benzende paraformaldehit ile reaksiyonu sonucunda kriptand [3.2.1] türünün ilk örnekleri elde edildi. Kriptand (2)’ nin Pd(CH3COO)2 ile (mediator) CH2Cl2/C6H6 (1/1) ortamındaki reaksiyonundan N,N′-bisformil [3.2] (BiBLE) lariat eter (3) sentezlendi. Kriptand ve BiBLE lariat eter bileşiklerinin yapısı, element analizi, MS, FT-IR, 1H-, 13C-NMR ve HETCOR spektrumundan yararlanılarak aydınlatıldı ve bu bileşikler için elde edilen spektroskopik veriler, dibenzo-diaza-taç eterler için elde edilen veriler ile karşılaştırıldı.

Keywords

Dibenzo-diaza-taç eterler BiBLE lariat eterler Kriptandlar

References

  • [1] Vögtle, F. and Weber, E., ‘‘Host guest complex chemistry III’’, Topics in Current in Chemistry, (Ed: Weber, E.), Springer, New York, 1-187 (1984).
  • [2] Winefordner, J.D., ‘‘Macrocyclic compounds in analytical chemistry’’, Chemical Analysis, Vol.143, John Wiley and Sons, New York, 1-424 (1997).
  • [3] Lindoy, L., ‘‘Heavy metal chemistry of mixed donor macrocyclic ligands: Strategies for obtaining metal ion recognition’’, Progress in Macrocyclic Chemistry, Vol. 3, John Wiley and Sons, New York, 53-97 (1987).
  • [4] Weber, E. and Vögtle, F., ‘‘Classification and nomenclature of coronands, cryptands, podands, and of their complexes’’, Inorg. Chim. Acta, 45: 65-67 (1980).
  • [5] Gokel, G.W., ‘‘Crown ethers and cryptands’’, Monographs in Supramolecular Chemistry, Coral Gables, Florida, U.S.A., 1-63 (1991).
  • [6] Goodwin, H.J., Henrick, K., Lindoy, L.F., McPartlin, M. and Tasker, P.A., ‘‘Studies of macrocylic ligand hole sizes. 1. X-ray structures of the nickel bromide complexes of the diimine and reduced forms of a 16-membered macrocyclic ring incorporating O2N2 donors’’, Inorg. Chem., 21: 3261-3264 (1982).
  • [7] Bilge, S., Kılıç, Z., Hökelek, T. and Erdoğan, B., ‘‘Complexes of Ni (II) and Pd (II) ions with 15- and 17-membered macrocycles containing O2N2- and O2N3-donors and the crystal structures of Ni(II) and Pd(II) complexes of 2,5-dioxa-13,16,19- triazatricyclo[19.4.0.06,11]-pentacosa-6,8,10,21,23,25(1)-hexaene’’, J. Mol. Struct., 691: 85-96 (2004).
  • [8] Adam, K.R., Clarkson, C., Leong A.J., Lindoy, L.F., McPartlin, M., Powell, H.R. and Smith, S.V., ‘‘Interaction of transition and post-transsition metal ions with oxygennitrogen donor macrocycles incorporating pendant hydroxyethyl and carbamoylethyl groups’’, J. Chem. Soc., Dalton Trans., 2791-2798 (1994).
  • [9] Hökelek, T., Kılıç, Z. and Bilge, S., ‘‘5,6,7,8,9,10,11,12,18,19,21,22-Dodecahydro- 8,9:18,19-dibenzo-1,4,7-trioxa-11,16-diazacyclononadeca-10,16-diene’’, Acta Cryst., C55: 381-383 (1999).
  • [10] Hökelek, T., Bilge, S., Akduran, N. and Kılıç, Z., ‘‘Crystal structure of 15,21- bis(diethoxyphosphinoyl)-2,5,8-trioxa-16,20-diazatricyclo [20.4.0.09,14] hexacosa-9,11,13,22,24,26(1)-hexaene-ethylphosphonic acid-water (1/1/1)’’, Cryst. Res. Technol., 36: 509-515 (2001).
  • [11] Bilge, S., Natsagdorj, A., Akduran, N., Hökelek, T. and Kılıç, Z., ‘‘C-bis-pivot podands and lariat ethers: Synthesis and spectral investigations. Structure of 15,21- bis{2-[(hydroxy)(methoxy)phosphoryl]}-2,5,8-trioxa-16,20-diazatricyclo[20.4.0.09,14] hexacosa-9,11,13,22,24,26(1)-hexaene-water (1/2)’’, J. Mol. Struct., 611: 169-178 (2002).
  • [12] Hökelek, T., Akduran, N., Bilge, S. and Kılıç, Z., ‘‘Crystal structure of 2,5-dioxa- 13,17-diazatricyclo[17.4.0.06,11]tricosa-6,8,10,12,17,19,21,23(1)-octaene’’, Anal. Sci., 18: 1065-1066 (2002).
  • [13] Hökelek, T., Bilge, S. and Kılıç, Z., ‘‘1,15-Diaza-3,4:12,13-dibenzo-5,8,11- trioxacycloheptadecane hemihydrate’’, Acta Cryst., E59: 1607-1609 (2003).
  • [14] Hökelek, T., Akduran, N., Bilge, S. and Kılıç, Z., ‘‘Crystal structure of3,4,6,7,15,16,17,18,19,20,21-undecahydro-2,5,6-trioxa-16,20-diazatricyclo [20.4.0.09,14]hexacosa-9,11,13,22,24,26(1)-hexaene’’, Anal. Sci., 17: 801-802 (2001).
  • [15] Hökelek, T., Akduran, N., Bilge, S. and Kılıç, Z., ‘‘Crystal structure of 3,4,6,7,15,16,17,18,19,20,21,27-dodecahydro-2,5,8-trioxa-16,20-diazatetracyclo [20.4.116,20.0.09,14]heptacosa-9,11,13,22,24,26(1)-hexaene’’, Anal. Sci., 17: 465-466 (2001).
  • [16] Adam, K.R., Leong, A.J., Lindoy, L.F., Lip, H.C., Skelton, B.W. and White, A.H., ‘‘Ligand design and metal-ion recognition. interaction of Ni(II) with 17- to 19- membered macrocycles containing O2N3 and O3N2 donor sets and the X-ray structure of the parent 17-membered macrocyclic ligand’’, J. Am. Chem. Soc., 105: 4645-4651 (1983).
  • [17] Hökelek, T., Kılıç, Z. and Bilge, S., ‘‘2,5,8-Trioxa-16,20-diazatricyclo [20.4.0.09,14]hexacosa-9,11,13,15,20,22,24,26-octaene’’, Acta Cryst., C55: 248-250 (1999).
  • [18] Zhang, J., Vittal, J., Henderson, W., Wheaton, J.R., Hall, I.H., Hor, T.S.A. and Yan, Y.K., ‘‘Tricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: Structures, solution behavior and cytotoxicity’’, J. Org. Chem., 650: 123-132 (2002).
  • [19] Hökelek, T., Yamak, İ. and Kılıç, Z., ‘‘Crystal structure of N,N,N′,N′- tetrakis(methyldiphenylphosphino)-bis(2′-phenoxy)-3,6 dioxaoctane’’, Anal. Sci., 19: 465-466 (2003).
  • [20] Dutasta, J.P., Declercq, J.P., Calderon, C.E. and Tinant, B., ‘‘Novel ditopic receptors based on the P2N2 diphosphazene ring; synthesis and X-ray structural characterizationof cis and trans bis(crown ether) annellated 1,3,2λ5,4λ5-diazadiphosphetidine-2,4 disulfide’’, J. Am. Chem. Soc., 111: 7136-7144 (1989).
  • [21] Yamak, İ., Lariat taç (crown) eterlerin ve komplekslerinin sentezi, yapılarının spektroskopik ve kristallografik yöntemler ile qydınlatılması, Doktora Tezi, Ankara Ünv. Fen Bilm. Ens., No.257 (2001).
  • [22] Kyba, E.P., Davis, R.E ., Hudson, C.W., John, A.M., Brown, S.B., McPaul, M.J., Liu, L. and Glover, C., ‘‘Tetradentate 14-membered tert-phosphino-containing macrocycles’’, J. Am. Chem. Soc., 103: 3868-3875 (1981).
  • [23] McLain, S.J., ‘‘Organometallic crown ethers. 1. Metal acyl binding to a crown ether held cation’’, J. Am. Chem. Soc., 105: 6355-6357 (1983).
  • [24] Power, P.P., Hope, H., Viggiano, M. and Moezzi, B., ‘‘Syntheses and X-ray crystal structures of two new classes of macrocyclic ligands having both phosphorus and nitrogen donor atoms’’, Inorg. Chem., 23: 2550-2552 (1984).
  • [25] Balch, A.L. and Rowley, S.P., ‘‘Sobulizing the thallium-platinum unit of Tl2Pt(CN)4. Preparation and use of a new crown ether / phoshine hybrid ligand for linking maingroup and transition-metal ions’’, J. Am. Chem. Soc., 112: 6139-6140 (1990).
  • [26] Lindoy, L.F., Skelton, B.W., Smith, S.V. and White, A.H., ‘‘New macrocyclic ligands. III. Pendant 2-pyridylmethyl of dibenzo-substituted O2N2-donor rings. The X-ray structure of a pendant 2-pyridylmethyl derivative’’, Aust. J. Chem., 46: 363-375 (1993).
  • [27] Bilge, S., Kılıç, Z., Çaylak, N. and Hökelek, T., ‘‘Phosphorus-nitrogen compounds: Novel spiro-crypta-phosphazenes. Structure of {pentane-3-oxa-N,N’-bis(1,5-oxybenzyl)-spiro(etane-1′,2′-diamino)-4,4,6,6-tetrachlorocyclo-2λ5,4λ5,6λ5- triphosphazatriene}. Part IX’’, J. Mol. Struct., 707: 139-146 (2004).
There are 27 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Articles
Authors

S. Bilge

Z. Kılıç

Publication Date May 15, 2006
Published in Issue Year 2006 Issue: 010

Cite

APA Bilge, S., & Kılıç, Z. (2006). KRİPTAND [3.2.1] VE N,N′-BİSFORMİL [3.2] LARİAT ETER LİGANDLARININ SENTEZİ VE YAPILARININ İNCELENMESİ. Journal of Science and Technology of Dumlupınar University(010), 33-44.
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