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Template synthesis of a rare 14-membered macrocyclic complex using cadmium(II) ion as a collector

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Abstract

In this work, a new macrocyclic cadmium complex, [Cd(ACE)I]2[CdI4] (1); ACE: 1,3,6,10,12,15-hexaazatricyclo[13.3.1.16,10]eicosane, was prepared by template method and characterized by elemental analysis, FT-IR spectroscopy and single-crystal X-ray diffraction. Structural analysis of the complex 1 revealed an ionic complex containing two cadmium atoms with tetrahedral (in anionic portion) and square-pyramidal (in cationic portion) geometries. Using the DFT calculations, thermodynamic stability of the first-row and group 12 metal complexes containing ACE ligand was investigated and then validated by comparing with the CSD analogues. Charge distribution pattern of ACE ligand was compared with cationic unit of 1 by NBO analysis to study of the charge variation of ligand after complexation.

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References

  1. Lv, F., Han, N., Qiu, Y., Liu, X., Luo, J., Li, Y.: Transition metal macrocycles for heterogeneous electrochemical CO2 reduction. Coord. Chem. Rev. 422, 213435 (2020)

    Article  CAS  Google Scholar 

  2. Kumar, A., Zhang, Y., Liu, W., Sun, X.: The chemistry, recent advancements and activity descriptors for macrocycles based electrocatalysts in oxygen reduction reaction. Coord. Chem. Rev. 402, 213047 (2020)

    Article  CAS  Google Scholar 

  3. Kim, N.-K., Sogawa, H., Takata, T.: Cu-tethered macrocycle catalysts: synthesis and size-selective CO2-fixation to propargylamines under ambient conditions. Tetrahedron Lett. 61, 151966 (2020)

    Article  CAS  Google Scholar 

  4. Ojha, B., Kumar, A., Thorat, K.G., Ravikanth, M.: Synthesis and studies of crowned dipyrromethenes based macrocycles. Tetrahedron 75(46), 130574 (2019)

    Article  CAS  Google Scholar 

  5. Beklemishev, M.K., Elshani, S., Wai, C.M.: Solvent extraction of radium with crown ether carboxylic acids. Anal. Chem. 66(20), 3521–3524 (1994)

    Article  CAS  Google Scholar 

  6. Fenton, D.E., Okawa, H.: Dalton perspectives. The emergence of trinuclear constellations at metallobiosites. J. Chem. Soc. Dalton Trans. 9, 1349–1357 (1993)

    Article  Google Scholar 

  7. Costamagna, J., Ferraudi, G., Matsuhiro, B., Campos-Vallette, M., Canales, J., Villagrán, M., Vargas, J., Aguirre, M.J.: Complexes of macrocycles with pendant arms as models for biological molecules. Coord. Chem. Rev. 196(1), 125–164 (2000)

    Article  CAS  Google Scholar 

  8. Wei, J., Jin, T.-T., Yang, J.-X., Jiang, X.-M., Liu, L.-J., Zhan, T.-G., Zhang, K.-D.: A tetrachloroazobenzene based macrocycle featuring with red-light regulated encapsulation for aryl dianionic guests. Tetrahedron Lett. 61(2), 151389 (2020)

    Article  CAS  Google Scholar 

  9. Hakimi, M., Moeini, K., Mardani, Z., Fernandes, M.A., Mohr, F., Schuh, E.: Template-directed synthesis of macrocyclic copper(II) complexes of diazacyclam, 1,3,6,10,12,15-hexaazatricyclo[13.3.1.16,10]eicosane. J. Coord. Chem. 65(7), 1232–1245 (2012)

    Article  CAS  Google Scholar 

  10. Allen, F.H.: The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr. B 58(3–1), 380–388 (2002)

    Article  PubMed  CAS  Google Scholar 

  11. Nakatani, Y., Furusho, Y., Yashima, E.: Synthesis of helically twisted [1 + 1]macrocycles assisted by amidinium-carboxylate salt bridges and control of their chiroptical properties. Org. Biomol. Chem. 11(10), 1614–1623 (2013)

    Article  CAS  PubMed  Google Scholar 

  12. Gregoliński, J., Lisowski, J., Lis, T.: New 2+2, 3+3 and 4+4 macrocycles derived from 1,2-diaminocyclohexane and 2,6-diformylpyridine. Org. Biomol. Chem. 3(17), 3161–3166 (2005)

    Article  PubMed  CAS  Google Scholar 

  13. Paćkowski, T., Gregoliński, J., Ślepokura, K., Lisowski, J.: 6 + 6 Macrocycles derived from 2,6-diformylpyridine and trans-1,2-diaminocyclohexane. Tetrahedron Lett. 59(41), 3669–3673 (2018)

    Article  CAS  Google Scholar 

  14. Gregoliński, J., Ślepokura, K., Paćkowski, T., Panek, J., Stefanowicz, P., Lisowski, J.: From 2 + 2 to 8 + 8 condensation products of diamine and dialdehyde: giant container-shaped macrocycles for multiple anion binding. J. Org. Chem. 81(13), 5285–5294 (2016)

    Article  PubMed  CAS  Google Scholar 

  15. Sheldrick, G.: A short history of SHELX. Acta Crystallogr. A 70(1), C1437 (2014)

    Article  Google Scholar 

  16. Sheldrick, G.: A short history of SHELX. Acta Crystallogr. A 64(1), 112–122 (2008)

    Article  CAS  PubMed  Google Scholar 

  17. Farrugia, L.J.: ORTEP-3 for Windows—a version ofORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr. 30(5–1), 565–565 (1997)

    Article  CAS  Google Scholar 

  18. Burnett, M.N., Johnson, C.K.: Ortep-III, Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge (1996)

  19. Bergerhof, G., Berndt, M., Brandenburg, K.: Evaluation of crystallographic data with the program DIAMOND. J. Res. Natl. Stand. Technol. 101(3), 221–225 (1996)

    Article  Google Scholar 

  20. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, N.J., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J.: Gaussian 09. Gaussian Inc, Wallingford (2009)

    Google Scholar 

  21. Perdew, J.P.: Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys. Rev. B 33(12), 8822–8824 (1986)

    Article  CAS  Google Scholar 

  22. Gregoliński, J., Ślepokura, K., Paćkowski, T., Lisowski, J.: Expansion of a 2 + 2 macrocycle into a 6 + 6 macrocycle: template effect of cadmium(II). Org. Lett. 16(17), 4372–4375 (2014)

    Article  PubMed  CAS  Google Scholar 

  23. Radecka-Paryzek, W., Luks, E.: The scandium(III) ion as a template for the synthesis of a hexaazaSchiff base macrocyclic ligand. Monatsh. Chem. 126(6–7), 795–798 (1995)

    Article  CAS  Google Scholar 

  24. Prasad, R.N., Mathur, M.: Synthesis and characterization of Cr(III), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes of 2,12-dimethyl-3-13-di-n-propyl-1,4,11,14-tetraazacycloeicosa-1,3,11,13-tetraene. J. Serb. Chem. Soc. 67, 825–832 (2002)

    Article  CAS  Google Scholar 

  25. Constable, E.C.: Metals and Ligand Reactivity: An Introduction to the Organic Chemistry of Metal Complexes, New, Revised and, expanded Wiley, New York (1995)

    Book  Google Scholar 

  26. Radecka-Paryzek, W., Patroniak, V., Lisowski, J.: Metal complexes of polyaza and polyoxaaza Schiff base macrocycles. Coord. Chem. Rev. 249(21), 2156–2175 (2005)

    Article  CAS  Google Scholar 

  27. Moeini, K.: Template-direct synthesis, characterization and crystal structure of macrocyclic copper(II) complexes and synthesis of copper(II) and silver(I) complexes with 2-hydroxybenzamide-based ligands and preparation of nano particles containing copper and silver by solvothermal method. Payame Noor University (2015)

  28. Chu, W., Wu, B., Tang, M., Fan, Y., Hou, H.: A novel dodecanuclear cadmium(II) macrocycle with a 3D framework: synthesis, structure and properties. CrystEngComm 14(13), 4414–4419 (2012)

    Article  CAS  Google Scholar 

  29. Hakimi, M., Vahedi, H., Rezvaninezhad, M., Schuh, E., Mohr, F.: Synthesis and characterization of copper(I) complexes from triphenylphosphine and isatin Schiff bases of semi- and thiosemicarbazide. J. Sulfur Chem. 32(1), 55–61 (2011)

    Article  CAS  Google Scholar 

  30. Addison, A.W., Rao, T.N., Reedijk, J., van Rijn, J., Verschoor, G.C.: Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper(II) perchlorate. J. Chem. Soc. Dalton Trans. 7, 1349–1356 (1984)

    Article  Google Scholar 

  31. Nazarenko, A.Y., Rusanov, E.B.: Molecular structure of cadmium iodide complexes with 5, 7, 7, 12, 14, 14-hexamethyl-1, 4, 8, 11-tetraazacyclotetradecane. Pol. J. Chem. 69, 1417 (1995)

    CAS  Google Scholar 

  32. Lim, I.-T., Suh, K.-A., Choi, K.-Y.: Synthesis and crystal structure of a chloro-bridged dinuclear cadmium(II) complex with 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane. Main Group Met. Chem. 34(1–2), 39–42 (2011)

    CAS  Google Scholar 

  33. Ito, H., Ito, T.: Structures of monomethylcarbonato- and hydrogencarbonato(1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane)cadmium(II) perchlorate, [Cd(O2COCH3)(Me4[14]aneN4)](ClO4) (I) and [Cd(O2COH)(Me4[14]aneN4)](ClO4) (II). Acta Crystallogr. C 41(11), 1598–1602 (1985)

    Article  Google Scholar 

  34. Dong, Y., Farquhar, S., Gloe, K., Lindoy, L.F., Rumbel, B.R., Turner, P., Wichmann, K.: Metal ion recognition. Interaction of a series of successively N-benzylated derivatives of 1,4,8,11-tetraazacyclotetradecane (cyclam) with selected transition and post-transition metal ions. Dalton Trans. 8, 1558–1566 (2003)

    Article  CAS  Google Scholar 

  35. Lim, I.-T., Choi, K.-Y.: Crystal structure of 3,14-dimethyl-2,6,13,17-tetraazatricyclo[14,4,01.18,07.12]docosane cadmium(II) chloride monohydrate. Main Group Met. Chem. 34(1–2), 5–6 (2011)

    CAS  Google Scholar 

  36. Kwag, J.-S., Jeong, M.-H., Lough, A.J., Kim, J.-C.: Investigation of molecular interactions in the carboxylato Zn(II) and Cd(II) macrocyclic complexes. Bull. Korean Chem. Soc. 31(7), 2069–2072 (2010)

    Article  CAS  Google Scholar 

  37. Zhang, H.-M., He, Y.-C., Yang, J., Liu, Y.-Y., Ma, J.-F.: Ten coordination polymers constructed using an unprecedented azamacrocyclic octacarboxylate ligand 1,4,8,11-tetrazacyclododecane-N, N′, N″, N‴-tetra-methylene-isophthalic acid: syntheses, structures, and photoluminescent properties. Cryst. Growth Des. 14(5), 2307–2317 (2014)

    Article  CAS  Google Scholar 

  38. Roy, T.G., Hazari, S.K.S., Barua, K.K., Anwar, N., Zukerman-Schpector, J., Tiekink, E.R.T.: Synthesis, characterization and anti-microbial studies of cadmium(II) compounds containing 3,10-C-meso-Me8[14]aneC. Crystal and molecular structure of cis-[CdLC(NO3)](NO3). Appl. Organomet. Chem. 24(12), 878–887 (2010)

    Article  CAS  Google Scholar 

  39. Al Shihadeh, Y., Benito, A., Lloris, J.M., Martínez-Máñez, R., Pardo, T., Soto, J., Marcos, M.D.: Polyaza and azaoxa macrocyclic receptors functionalised with fluorescent subunits; Hg2+ selective signalling. J. Chem. Soc. Dalton Trans. 7, 1199–1205 (2000)

    Article  Google Scholar 

  40. Choi, K.-Y., Suh, M., Kim, J., Choo, G.-H., Suh, I.-H., Ng, S.W.: Crystal structure of a cadmium(II)terephthalate-3,14-dimethyl- 2,6,13,17-tetraazatricyclo[14,4,01.18,07 12]docosane dihydrate. Main Group Met. Chem. 24(2), 119–122 (2001)

    Article  Google Scholar 

  41. Chen, C.H., Cai, J., Liao, C.Z., Feng, X.L., Chen, X.M., Ng, S.W.: Variation in the coordination mode of arenedisulfonates: syntheses and structural characterization of mononuclear and dinuclear cadmium(II) arenedisulfonate complexes with two- to zero-dimensional architectures. Inorg. Chem. 41(19), 4967–4974 (2002)

    Article  CAS  PubMed  Google Scholar 

  42. Liang, X., Parkinson, J.A., Parsons, S., Weishaupl, M., Sadler, P.J.: Cadmium cyclam complexes: interconversion of cis and trans configurations and fixation of CO(2). Inorg. Chem. 41(17), 4539–4547 (2002)

    Article  CAS  PubMed  Google Scholar 

  43. Roy, T.G., Hazari, S.K., Nath, B.C., Ng, S.W., Tiekink, E.R.: cis-(Nitrato-kappa(2)O, O’)(2,5,5,7,9,12,12,14-octa-methyl-1,4,8,11-tetra-aza-cycl o-tetra-decane-kappa(4)N, N’, N", N"’)cadmium nitrate hemihydrate. Acta Crystallogr. E68(Pt 4), m494-495 (2012)

    Google Scholar 

  44. Hakimi, M., Moeini, K., Mardani, Z., Mohr, F.: Microwave-assisted template synthesis of diazacyclam-based macrocyclic copper complex and forming octahedral, square planar and square pyramidal geometries by ion exchanging and introducing a novel 2D square-grid copper–mercury coordination polymer. Polyhedron 70, 92–100 (2014)

    Article  CAS  Google Scholar 

  45. Hakimi, M., Mardani, Z., Moeini, K., Mohr, F.: Coordination behavior of dimethyl pyridine-2,6-dicarboxylate towards mercury(II), cadmium(II) and chromium(III) in the solid- and gaseous state supported by CSD studies. Polyhedron 102, 569–577 (2015)

    Article  CAS  Google Scholar 

  46. Mardani, Z., Moeini, K., Darroudi, M., Carpenter-Warren, C., Slawin, A.M.Z., Woollins, J.D.: Macrocyclic copper(II) complexes containing diazacyclam-based ligand: spectral, structural and docking studies. J. Coord. Chem. 72(18), 3030–3045 (2019)

    Article  CAS  Google Scholar 

  47. Hakimi, M., Mardani, Z., Moeini, K., Mohr, F.: Synthesis and characterization of a macrocyclic copper complex containing the 14-membered 1,3,5,8,10,12-hexaazacyclotetradecane unit. Z. Naturforsch. 72B(2), 115–118 (2017)

    Article  CAS  Google Scholar 

  48. Marandi, F., Moeini, K., Arkak, A., Mardani, Z., Krautscheid, H.: Docking studies to evaluate the biological activities of the Co(II) and Ni(II) complexes containing the triazine unit: supported by structural, spectral, and theoretical studies. J. Coord. Chem. 71(23), 3893–3911 (2019)

    Article  CAS  Google Scholar 

  49. Marandi, F., Moeini, K., Alizadeh, F., Mardani, Z., Quah, C.K., Loh, W.-S., Woollins, J.D.: Treatment of cadmium(II) and zinc(II) with N 2 -donor linkages in presence of β -diketone ligand; supported by structural, spectral, theoretical and docking studies. Inorg. Chim. Acta 482, 717–725 (2018)

    Article  CAS  Google Scholar 

  50. Mardani, Z., Golsanamlou, V., Khodavandegar, S., Moeini, K., Slawin, A.M.Z., Woollins, J.D.: The coordination of a multidentate NxOy-donor (x and y ≤ 2) oxazolidine-based ligand with Cd(II) and Hg(II); Structural, spectral, and theoretical studies. J. Coord. Chem. 71(1), 120–134 (2018)

    Article  CAS  Google Scholar 

  51. Marandi, F., Moeini, K., Mostafazadeh, B., Krautscheid, H.: Structural, spectral and theoretical aspects in the coordination of a triazine-based ligand toward lead(II) with a holodirected environment. Polyhedron 133, 146–154 (2017)

    Article  CAS  Google Scholar 

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Acknowledgements

We would like to acknowledge the FAIRE (Frank H. Allen International Research and Education Programme) award of the Cambridge Structural Database, for supplying access to the CSD softwares package.

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Authors and Affiliations

  1. Inorganic Chemistry Department, Faculty of Chemistry, Urmia University, 57561-51818, Urmia, Islamic Republic of Iran

    Sima Dorjani & Zahra Mardani

  2. Chemistry Department, Payame Noor University, 19395-4697, Tehran, Islamic Republic of Iran

    Keyvan Moeini

  3. EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK

    Cameron Carpenter-Warren

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  1. Sima Dorjani
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Dorjani, S., Mardani, Z., Moeini, K. et al. Template synthesis of a rare 14-membered macrocyclic complex using cadmium(II) ion as a collector. J Incl Phenom Macrocycl Chem 102, 523–531 (2022). https://doi.org/10.1007/s10847-022-01136-3

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