The Synthesis of Diamidediallylcalix[4]arene Derivatives as Ligand for Bromide Anion

Aliia S. Gusak, Polina E. Prokhorova, Yuri Yu. Morzherin^@

Ural Federal University, 620002 Ekaterinburg, Russian Federation

^@Corresponding author E-mail: yu.yu.morzherin@urfu.ru

Alkylation reaction of 5,17-diallylcalix[4]arene by the N-alkyl and N-aryl amides of chloroacetic acid was performed. NMR and UV titration of calix[4]arenes by bromide anion were carried out. It was shown that complex calixarene:bromide 2:1 was formed. The calixarene containing two n-butylamide moieties was determined to possess the most significant binding constant among all examined compounds.

References:

Click here to expand or collapse this section

1. Pasquale S., Sattin S., Escudero-Adan E.C., Martinez-Belmonte M., de Mendoza J. Nature Commun. 2012, 3 1–7.
http://dx.doi.org/10.1038/ncomms1793

2. Dasary H., Jagan R., Chand D.K. Chem. Eur. J. 2015, 21, 1499 – 1507.
http://dx.doi.org/10.1002/chem.201405255

3. Aydogan A., Lee G., Lee C.-H., Sessler J.L. Chem. Eur. J. 2015, 21, 2368 – 2376.
http://dx.doi.org/10.1002/chem.201404421

4. Zheng G., Chen M., Liu X., Zhou J., Xie J., Diao G. Electrochimica Acta 2014, 136, 301–309.
http://dx.doi.org/10.1016/j.electacta.2014.05.086

5. Chawla H.M., Kar J.R., Siddiqui W.A., Kumar N., Black D.S. Tetrahedron Lett. 2014, 55, 4517–4520.
http://dx.doi.org/10.1016/j.tetlet.2014.06.044

6. Chawla H.M., Goel P., Munjal P. Tetrahedron Lett. 2015, 56, 682–685.
http://dx.doi.org/10.1016/j.tetlet.2014.12.057

7. Mummidivarapua V.V.S., Pathaka R.K., Hingeb V.K., Dessingoua J., Rao C.P. Supramol. Chem. 2014, 26, 538–546.
http://dx.doi.org/10.1080/10610278.2013.868897

8. Mutihac L., Enache I.V., Diacu E., Mutihac R.-C., Vicens J. Supramol. Chem. 2014, 26, 521–525.
http://dx.doi.org/10.1080/10610278.2013.863315

9. He X., Fan J., Zhang F., Li R., Pollack K.A., Raymond J.E., Zou J., Wooley K.L. J. Mater. Chem. B 2014, 2, 8123–8130.
http://dx.doi.org/10.1039/C4TB00909F

10. Haupt S., Handke M., Kuhnert R., Poetsch M., Kersting B. Tetrahedron 2014, 70, 5254–5259.
http://dx.doi.org/10.1016/j.tet.2014.05.075

11. Liu Y., Hao Z., Lv S., Huang J., Liao C., Run M. Polymer 2015, 57, 29–38.
http://dx.doi.org/10.1016/j.polymer.2014.12.005

12. Gusak A. S., Ivanova E. A., Prokhorova P. E., Rusinov G. L., Verbitskiy E. V., Morzherin Yu. Yu. Russ. Chem. Bull. 2014, 63, 1395–1398.
http://dx.doi.org/10.1007/s11172-014-0609-4

13. Gładkowski W., Skrobiszewski A., Mazur M., Siepka M., Białońska A. Eur. J. Org. Chem. 2015, 605–615.
http://dx.doi.org/10.1002/ejoc.201403343

14. Deng W.-H.,Ye F.,Bai X.-F.,Zheng Z.-J.,Cui Y.-M.,Xu L.-W.ChemCatChem 2015, 7, 75–79.
http://dx.doi.org/10.1002/cctc.201402733

15. Rapi Z., Bakó P., Drahos L., Keglevich G. Heteroatom Chem. 2015, 26, 63–71.
http://dx.doi.org/10.1002/hc.21214

16. Haupt S., Handke M., Kuhnert R., Poetsch M., Kersting B. Tetrahedron 2014, 70, 5254–5259.
http://dx.doi.org/10.1016/j.tet.2014.05.075

17. Pitarch M., McKee V., Nieuwenhuyzen M., McKervey M.A. J. Org. Chem. 1998, 63, 946–951.
http://dx.doi.org/10.1021/jo970887q

18. Ozkan S.C., Yilmaz A., Arslan E., Acik L., Sayin U., Mutlu E.G. Supramol. Chem. 2015, 27, 255–267.
http://dx.doi.org/10.1080/10610278.2014.978868

19. Ansari S.A., Mohapatraa P.K., Iqbal M.I., Huskens J., Verboom W. J. Chromatography A 2014, 1334, 79–86.
http://dx.doi.org/10.1016/j.chroma.2014.02.009

20. Hung H.-C., Chang Y.-Y., Luo L., Hung C.-H., Diau E.W.-G., Chung W.-S. Photochem. Photobiol. Sci. 2014, 13, 370–379.
http://dx.doi.org/10.1039/c3pp50175b

21. Cafeo G., Gattuso G., Kohnke F.H., Papanikolaou G., Profumo A., Rosano C. Chem. Eur. J. 2014, 20, 1658–1668.
http://dx.doi.org/10.1002/chem.201303265

22. Kulyashova A.E., Geide I.V., Prokhorova P.E., Morzherin Yu.Yu. Russ. J. Org. Chem. 2014, 50, 565–570.
http://dx.doi.org/10.1134/S1070428014040216

23. Methodical instruction 4.1.2587-10 Spectrophotometrical determination of bromide ions in the drinking water (in Russ.).

24. Zhaowen L., Li Z., Chunfen X., Yong Y., Fanbo Z., Kaixun H. Med. Chem. Res. 2007, 16, 380–391.
http://dx.doi.org/10.1007/s00044-007-9050-7

25. van Loon J.-D., Arduini A., Coppi L., Verboom W., Pochini A., Ungaro R., Harkema S., Reinhoudt D.N. J. Org. Chem. 1990, 55, 5639–5646.
http://dx.doi.org/10.1021/jo00308a024

26. Dondoni A., Kleban M., Hu X., Marra A., Banks H.D. J. Org. Chem. 2002, 67, 4722–4733.
http://dx.doi.org/10.1021/jo020178z

27. Pitarch M., McKee V., Nieuwenhuyzen M., McKervey M.A. J. Org. Chem. 1998, 63, 946–951.
http://dx.doi.org/10.1021/jo970887q

28. Hu X.-Y., Peng S., Guo D.-S., Ding F., Liu Y. Supramol. Chem. 2015, 27, 336-345.
http://dx.doi.org/10.1080/10610278.2014.967242

29. Mendez-Arroyo J., Barroso-Flores J., Lifschitz A.M., Sarjeant A.A., Stern C.L., Mirkin C.A. J. Am. Chem. Soc. 2014, 136, 10340−10348.
http://dx.doi.org/10.1021/ja503506a

30. Gaeta C., Talotta C., Sala P.D., Margarucci L., Casapullo A., Neri P. J. Org. Chem. 2014, 79, 3704−3708.
http://dx.doi.org/10.1021/jo500422u

31. Hirose K. Determination of Binding Constants In: Analytical Methods in Supramolecular Chemistry, Chapter 2; (Schalley C., Ed.), Weinheim, Germany: Wiley-VCH, 2006, 17−54.
http://dx.doi.org/10.1002/9783527610273.ch2

Attachment	Size
mhc150351m.pdf	687.99 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

The Synthesis of Diamidediallylcalix[4]arene Derivatives as Ligand for Bromide Anion

References: