FT-IR and FT-Raman study of hydrogen bonding in p-alkylcalix[8]arenes

Abstract

The FTIR and FT Raman spectra of p-alkylcalix[8]arenes (alkyl = tert-butyl, isononyl) were recorded. Analysis of IR spectra showed that the cyclic cooperative intramolecular hydrogen bond is realized in calix[8]arene. It was found that the strength of the cyclic cooperative intramolecular hydrogen bond in the series of alkyl derivatives of calix[8]arenes depends very little on the replacement of the p-tert-butyl groups by the more bulky isononyl group. From our data follows that the orientation of aromatic fragments in calixarene molecules depends on the type of alkyl substituent.An analysis of the changes in the IR spectra with heating and dissolution shows that the conformation of the “pleated-loop” is retained in p-tert-butylcalix[8]arene. It turned out that the intramolecular hydrogen bond is a “probe” of the conformation of calixarene molecules and IR spectroscopy is a unique method that allows one to follow the slightest nuances of changes in the H-bound system of these supermolecules.