The study of calixarenes complexation with phenols by RP HPLC

Authors

  • O. I. Kalchenko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • S. O. Cherenok Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • A. V. Solovyov University of California, United States
  • S. Yu. Suikov Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • V. I. Kalchenko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.17.910

Keywords:

Calixarenes, phenols, inclusion complexes, binding constants, molecular modeling

Abstract

The Host-Guest complexation of octakis(diphenoxyphosphoryloxy)tetramethylcalix[4]resorcinarene, 5,17-bis-(N-tolyliminomethyl)-25,27-dipropoxycalix[4]arene and 5,11,17,23-tetrakis(diisopropoxyphosphonyl)-25,26,27,28-tetrapropoxycalix[4]arene with a series of 11 phenols (phenol, p-fluorophenol, p-chlorophenol, p-bromophenol, pyrogallol, p-cresol, p-aminophenol, p-nitrophenol, salicylic aldehyde, guaiacol and veratrole) has been studied by the high-performance liquid chromatography (RP HPLC) method. Chromatographic characteristics and log P of industrial phenols have been determined. Using the relationship of the phenol retention factor k’ vs the calixarene concentration in the mobile phase the stability constants of the supramolecular complexes KA (29-331 M-1) have been determined. The stability constants of the calixarene complexes show that the Host-Guest interaction strongly depends on the nature of the substituents in the Host and Guest molecules. Calixresorcinarene functionalized by diphenoxyphosphoryl groups and calixarene containing tolyliminomethyl groups formed more stable complexes with some phenols compared to calixarene functionalized by diisopropoxyphosphonyl groups. In accordance with the molecular modeling data the complexation does not change the C2v flattened-cone conformation of the calixarene skeleton. The Host-Guest complexes are stabilized by the intermolecular hydrogen bonds of phenolic OH groups with oxygen atoms of P = O groups at the upper rim, and OH groups at the lower rim of the macrocycle. Hydrophobic interactions also participate in the complexation. 

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Published

2017-03-23

How to Cite

(1)
Kalchenko, O. I.; Cherenok, S. O.; Solovyov, A. V.; Suikov, S. Y.; Kalchenko, V. I. The Study of Calixarenes Complexation With Phenols by RP HPLC. J. Org. Pharm. Chem. 2017, 15, 45-51.

Issue

Vol. 15 No. 1(57) (2017)

Section

Original Researches

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