Journal of the Korean Magnetic Resonance Society (한국자기공명학회논문지)

Korean Magnetic Resonance Society (한국자기공명학회)
권호 표지
DOI QR코드

DOI QR Code

H-D exchange of pyrrolic NH protons prompted by fluoride in aprotic DMSO-d6

  • Sung Kuk Kim (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
  • Received : 2024.11.12
  • Accepted : 2024.11.28
  • Published : 2024.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

The binding feature of bipyrrole-strapped calix[4]pyrrole 1 for the fluoride anion was examined by a combination of 1H and 19F NMR spectroscopy in DMSO-d6 . Receptor 1 was found to bind the fluoride anion with high affinity via two step-process. Fluoride binding to receptor 1 was proved to facilitate deuterium exchange of the pyrrolic protons in the nominally aprotic deuterated solvent of DMSO-d6.

Keywords

Acknowledgement

This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (NRF-2022R1A4A1021817 to S.K.K.).

References

  1. J. L. Sessler, P. A. Gale, W.-S. Cho, Anion Receptor Chemistry; Stoddart, J. F., Ed; Royal Society of Chemistry: Cambridge (2006)
  2. P. D. Beer and P. A. Gale, Angew Chem., Int. Ed. 40, 486 (2001).
  3. P. A. Gale, N. Busschaert, C. J. E. Haynes, L. E. Karagiannidis, and I. L. Kirby, Chem. Soc. Rev. 43, 205
  4. S. O. Kang, R. A. Begum, and K. Bowman-James, Angew. Chem., Int. Ed. 45, 7882 (2006)
  5. Y. Zhou, J. F. Zhang, and J. Yoon, Chem. Rev. 114, 5511 (2014)
  6. M. Cametti and K. Rissanen, Chem. Soc. Rev. 42, 2016 (2013).
  7. A. Brugnara, F. Topic, K. Rissanen, A. de la Lande, B. Colasson, and O. Reinaud, Chem. Sci. 5, 3897 (2014). 8. L. W. Ripa, J. Publ. Health Dent. 53, 17 (1993)
  8. L. W. Ripa, J. Publ. Health Dent. 53, 17 (1993)
  9. M. S. McDonagh, P. F. Whiting, P. M. Wilson, A. J. Sutton, I. Chestnutt, J. Cooper, K. Misso, M. Bradley, E. Treasure, and J. Kleijnen, Br. Med. J. 321, 855 (2000)
  10. P. Connet, Fluoride 40, 155 (2007)
  11. L. K. Kirk, Biochemistry of the Halogens and Inorganic Halides; Plenom Press: New York (1991)
  12. M. Kleerekoper, Endocrinol. Metab. Clin. North Am. 27, 441 (1998)
  13. E. Gazzano, L. Bergandi, C. Riganti, E. Aldieri, S. Doublier, C. Costamagna, A. Bosia, and D. Ghigo, Curr. Med. Chem. 17, 2431 (2010)
  14. O. Barbier, L. Arreola-Mendoza, and L. M. Del Razo, Chem.–Biol. Interact. 188, 319 (2010).
  15. C.-H. Lee, H. Miyaji, D.-W. Yoon, and J. L. Sessler, Chem. Commun. 24 (2008)
  16. S. K. Kim and J. L. Sessler, Acc. Chem. Res. 47, 2525 (2014)
  17. S. Peng, Q. He, G. I. Vargas-Zuniga, L. Qin, I. Hwang, S. K. Kim, N. J. Heo, C,-H. Lee, R. Dutta, and J. L. Sessler, Chem. Soc. Rev. 49, 865 (2020)
  18. S. O. Kang, J. M. Llinares, D. Powell, D. VanderVelde, and Bowman-James, K. J. Am. Chem. Soc. 125, 10152 (2003)
  19. S. O. Kang, D. VanderVelde, D. Powell, and K. Bowman-James, J. Am. Chem. Soc. 126, 12272 (2004)
  20. Q.-Q Wang, V. W. Day, and K. Bowman-James, Angew. Chem., Int. Ed. 51, 2119 (2012).
  21. S. K. Kim, J. Lee, N. J. Williams, V. M. Lynch, B. P. Hay, B. A. Moyer, and J. L. Sessler, J. Am. Chem. Soc. 136, 15079 (2014)
  22. Approximate binding constant from: K, A. Connors, Binding Constants: The Measurement of Molecular Complex Stability; Wiley-Interscience: New York (1987)