Skip to main content
SpringerLink
Log in

Computational insight towards the binding affinity and participation of aliphatic unsaturated sidearms of aza-18-crown-6 extractants for Sr2+ encapsulation in different solvent medium

  • Original Paper
  • Published:
Journal of Molecular Modeling Aims and scope Submit manuscript

Abstract

Context

Macrocyclic extractants capture cations in solution phase; therefore, their structures and energetics in different solvents are worth investigating. In this computational research work, the optimized geometry of three aza-18-crown-6 extractants (1–3) has been obtained in suitable solvent mediums to work out the influence of the solvation on their binding affinity with Sr2+. The designed macrocyclic extractants are remarkable as the N-substituted side chain bears the rarely examined simple aliphatic unsaturated double and triple bond. All significant structural perturbations of the macro ring wherein Sr2+ binds are examined. Prediction of the auxiliary effect of the simple aliphatic unsaturated side arm on the binding of Sr2+ through solvent competition or cation-pi interaction is undertaken. The binding affinity of the complex formed in the solvent and gas phases is calculated. Results obtained in this study favor the utilization of solvents of low dielectric constant (CHCl3 and DCM) for effective binding of Sr2+ ions by the extractants.

Method

All DFT calculations were performed using the Gaussian 09 program. The optimized geometries and their structural features were visualized by GaussView. Density functional calculation involving B3LYP functional and LANL2DZ basis set was employed to obtain optimized geometry and energy of the extractants and their Sr2+ complex. The solvation effects were considered by employing the calculations with the polarized continuum model (PCM). The computational method’s reliability was assured by comparing the optimized structure with that of X-ray reported structure of a similar type of complex.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Data Availability

All data generated or analyzed during this study are included in this published article and its supplementary material.

References

  1. Macmillan JP, Park JW, Gerstenberg R, Wagner H, Köhler K, Wallbrecht P (2012) Ullman’s encyclopedia of industrial chemistry, strontium and strontium compounds, vol 34. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA, pp 473–480

    Google Scholar 

  2. Hibbins SG and Updated by Staff (2013) Kirk-Othmer Encycl Chem Technol:1–10

  3. https://www.iea.org/policies/15274-the-2020-eu-critical-raw-materials-list. Accessed 07 Jun 2023

  4. https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:52020DC0474. Accessed 07 Jun 2023

  5. Ober JA (2013) Strontium, U.S. geological survey, http://minerals. usgs.gov/minerals/pubs/commodity/strontium/myb1-2013-stron.pdf. Accessed 07 Jun 2023

  6. Mason B, Moore CB (1985) Grundzuge der Geochemie €. Enke Verlag, Stuttgart

    Google Scholar 

  7. Rebary B, Raichura M, Mangukia S, Patidar R (2014) Mapping of iodine, lithium and strontium in oil-field water of Cambay basin, Gujarat. J Geol Soc Ind 83:669–675. https://doi.org/10.1007/s12594-014-0098-y

    Article  CAS  Google Scholar 

  8. https://www.iaea.org/sites/default/files/21/10/nuclear-energy-for-a-net-zero-world.pdf. Accessed 07 June 2023

  9. Brumfiel G (2011) Fukushima set for epic clean-up. Nature 472(7342):146–147

    Article  CAS  PubMed  Google Scholar 

  10. Wilson PD (1996) The nuclear fuel cycle: From ore to wastes. Oxford University Press, Oxford

    Google Scholar 

  11. Choppin G, Liljenzin JO, Rydberg J (2002) Radiochemistry and nuclear chemistry. Butterworth-Heinemann

    Google Scholar 

  12. Pedersen CJ (1967) Cyclic polyethers and their complexes with metal salts. J Am Chem Soc 89(26):7017–7036

    Article  CAS  Google Scholar 

  13. Guo C, Yuan M, He L, Cheng L, Wang X, Shen N, Wang S et al (2021) Efficient capture of Sr2+ from acidic aqueous solution by an 18-crown-6-ether-based metal organic framework. CrystEngComm 23(18):3349–3355

    Article  CAS  Google Scholar 

  14. Deb AS, Manju M, Sengupta A, Ali SM (2022) Efficient separation of strontium ions from aqueous solution by dibenzo-18-crown-6 functionalized resin: static and dynamic adsorption studies with computational DFT insights. Chem Eng J Adv 11:100308

    Article  CAS  Google Scholar 

  15. Mu W, Du S, Li X, Yu Q, Hu R, Wei H, Yang Y, Peng S (2019) Efficient and irreversible capture of strontium ions from aqueous solution using metal–organic frameworks with ion trapping groups. Dalton Trans 48(10):3284–3290

    Article  CAS  PubMed  Google Scholar 

  16. Bradshaw JS, Izatt RM, Bordunov AV, Zhu CY, Hathaway JK, Gokel GW (1996) Comprehensive supramolecular chemistry. Pergammon, New York

    Google Scholar 

  17. Gokel G (1991) Crown ethers and cryptands. Monogr Supramol Chem Series:115–117

  18. Gokel GW, Atwood IJ, Steed J (eds) (2004) Encyclopedia of supramolecular chemistry. Marcel Dekker, New York, pp 326–333

    Book  Google Scholar 

  19. Bai F, He C, Chen G, Wei J, Wang J, Ye G (2013) Synthesis of alkyl substituted dicyclohexano-18-crown-6 homologues for strontium extraction in HNO3 media. Energy Proc 39:396–402

    Article  CAS  Google Scholar 

  20. Blasius E, Klein W, Schön U (1985) Separation of strontium from nuclear waste solutions by solvent extraction with crown ethers. J Radioanal Nucl Chem 89:389–398

    Article  CAS  Google Scholar 

  21. Kumar A, Mohapatra PK, Manchanda VK (1999) Extraction of radiostrontium from nitric acid mediumusing di-t-Butyl cyclohexano 18crown6in an aliphatic alcohol mixture diluent. Radiochim Acta 85(3-4):113–118

    Article  CAS  Google Scholar 

  22. Boda A, Joshi JM, Ali SM, Shenoy KT, Ghosh SK (2013) Density functional theoretical study on the preferential selectivity of macrocyclic dicyclohexano-18-crown-6 for Sr+2 ion over Th+4 ion during extraction from an aqueous phase to organic phases with different dielectric constants. J Mol Model 19:5277–5291

    Article  CAS  PubMed  Google Scholar 

  23. Horwitz EP, Dietz ML, Fisher DE (1990) Extraction of stoontium from nitric acid solutions using dicyclohexano-18-crown-5 and its derivatives. Solvent Extr Ion Exch 8(4-5):557–572

    Article  CAS  Google Scholar 

  24. Kumar A, Mohapatra PK, Pathak PN, Manchanda VK (1997) Dicyclohexano 18 crown 6 in butanol-octanol mixture: a promising extractant of Sr(II) from nitric acid medium. Talanta 45(2):387–395

    Article  CAS  PubMed  Google Scholar 

  25. Boda A, Ali SM, Shenoi MR, Rao H, Ghosh SK (2011) DFT modeling on the suitable crown ether architecture for complexation with Cs+ and Sr2+ metal ions. J Mol Model 17:1091–1108

    Article  CAS  PubMed  Google Scholar 

  26. Bezhin NA, Dovhyi II (2015) Sorbents based on crown ethers: preparation and application for the sorption of strontium. Russ Chem Rev 84(12):1279

    Article  CAS  Google Scholar 

  27. Zhang A, Xiao C, Liu Y, Hu Q, Chen C, Kuraoka E (2010) Preparation of macroporous silica-based crown ether materials for strontium separation. J Porous Mater 17:153–161

    Article  CAS  Google Scholar 

  28. Schultz RA, Dishong DM, Gokel GW (1981) Lariat ethers. 3. Macrocylic polyethers bearing donor groups on flexible arms attached at a nitrogen pivot point. Tetrahedron Lett 22(28):2623–2626

    Article  CAS  Google Scholar 

  29. Arnold KA, Viscariello AM, Kim M, Gandour RD, Fronczek FR, Gokel GW (1988) N, N'-Bis (subst1tuted)-4, 13-diaza-18-crown-6 derivatives having pi-donor-group-sidearms: correlation of thermodynamics and solid state structures. Tetrahedron Lett 29(25):3025–3028

    Article  CAS  Google Scholar 

  30. De Wall SL, Barbour LJ, Gokel GW (1999) Cation-π complexation of potassium cation with the phenolic sidechain of tyrosine. J Am Chem Soc 121(36):8405–8406

    Article  Google Scholar 

  31. Hu J, Barbour LJ, Gokel GW (2001) Solid state evidence for π-complexation of sodium cation by carbon–carbon double bonds. Chem Comm 18:1858–1859

    Article  Google Scholar 

  32. Hu J, Barbour LJ, Gokel GW (2001) Solid-state evidence for Pi-complexation of sodium and potassium cations by carbon− carbon triple bonds. J Am Chem Soc 123(38):9486–9487

    Article  CAS  PubMed  Google Scholar 

  33. Obrai S, Kumar R, Goyal M, Kaushal S (2016) DFT studies of calcium (II), strontium (II) and barium (II) benzoates with N,N,N′,N′-Tetrakis (2-hydroxyethyl/propyl) ethylenediamine. J Mol Struct 1113:18–23

    Article  CAS  Google Scholar 

  34. Marijana H, Branislav M, Mihajlo E, Milena P (2023) Decorated crown ethers as selective ion traps: Solvent’s role in crown’s preference towards a specific ion. J Mole Liq 381:121791

    Article  Google Scholar 

  35. Yahya N, Ergin K, Burcu A, Nurgül S, Hasan A, Zeynel S (2021) New naphthoquinone-imidazole hybrids: Synthesis, anion recognition properties, DFT studies and acid dissociation constants. J Mole Liq 327:114855

    Article  Google Scholar 

  36. Kacie JN, Paige JB, Holly ER, Kana T (2019) Divergent excited state proton transfer reactions of bifunctional photoacids 1-ammonium-2- naphthol and 3-ammonium-2-naphthol in water and methanol. Phys Chem Chem Phys 21:24383–24392

    Article  Google Scholar 

  37. Musleh UM, Giel B, Jos O (2022) Facial vs. meridional coordination in gaseous Ni(II)-hexacyclen complexes revealed with infrared ion spectroscopy. Phys Chem Chem Phys 24:26890–26897

    Article  Google Scholar 

  38. Alex WJB, Yu L, Matthew PS, Iñigo JVY, Claire LM, Fabrizio O (2023) A blueprint for the stabilization of sub-valent alkaline earth complexes. Chem Eur J:e202301850

  39. Barbour LJ, De Wall SL, Ferdani R, Fronczek FR, Gokel GW (2001) Intermolecular axial solvation of bound cations by sidearm donor groups in lariat ethers: formation of a supramolecular network. Inorganica Chim Acta 317(1-2):121–126

    Article  CAS  Google Scholar 

  40. Horwitz EP, Dietz ML, Fisher DE (1991) SREX: a new process for the extraction and recovery of strontium from acidic nuclear waste streams. Solvent Extr Ion Exch 9(1):1–25

    Article  CAS  Google Scholar 

  41. Patidar R, Paul P, Ganguly B (2013) Probing the influence of solvent effect on the lithium ion binding affinity of 12-crown-O3N derivatives with unsaturated side arms: a computational study. J Mol Graph Model 46:22–28

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The fruitful discussions with experienced computational chemists are highly acknowledged. This research work has not received any specific grant. Improvement of this paper would not have happened without the comments and suggestions of the anonymous reviewers. Therefore, the authors are highly thankful to them for their valuable contribution.

Author information

Authors and Affiliations

  1. CSIR-Advanced Materials and Processes Research Institute, Bhopal, Madhya Pradesh, 462026, India

    Rajesh Patidar

  2. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

    Rajesh Patidar, Hariom Gupta & Aman Savita

  3. CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow, 226015, India

    Hariom Gupta & Aman Savita

Authors
  1. Rajesh Patidar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hariom Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aman Savita
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

All authors contributed to the conceptualization and design of the problem. Rajesh Patidar and Hariom Gupta performed material preparation, data collection, and analysis. Aman Savita did formatting, editing, and analysis. Rajesh Patidar wrote the first draft of the manuscript, and all authors commented on previous versions. All authors read and approved the final manuscript.

Corresponding authors

Correspondence to Rajesh Patidar or Hariom Gupta.

Ethics declarations

Ethics approval

No applicable.

Competing interests

The authors have no competing interests to declare that are relevant to the content of this article.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

ESM 1

(DOCX 2.67 mb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patidar, R., Gupta, H. & Savita, A. Computational insight towards the binding affinity and participation of aliphatic unsaturated sidearms of aza-18-crown-6 extractants for Sr2+ encapsulation in different solvent medium. J Mol Model 29, 294 (2023). https://doi.org/10.1007/s00894-023-05701-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00894-023-05701-6

Keywords

Search

Navigation