Deprotonation of calixarenes in acetonitrile.

@article{Cunningham2005DeprotonationOC,
  title={Deprotonation of calixarenes in acetonitrile.},
  author={Ian D Cunningham and Marc Woolfall},
  journal={The Journal of organic chemistry},
  year={2005},
  volume={70 23},
  pages={9248-56}
}
[Structure: see text]. The pKa values for calixarenes in MeCN have been determined by selective titration with bases using a spectroscopic method. These values are as follows: calix[4]arene pKa(1) = 19.06 +/- 0.22, pKa(2) > 33; calix[6]arene pKa(1) = 15.59 +/- 0.06, pKa(2) = 23.85 +/- 0.35, pKa(3) > 33; calix[8]arene pKa(1) = 17.20 +/- 0.20, pKa(2) = 20.32 +/- 0.31, pKa(3) > 33. The trends in acidity are rationalized using structures generated by a DFT model. For mono-deprotonation, the degree… CONTINUE READING