A general mode to obtain endo-complexation and through-the-annulus threading of scarcely efficient macrocyclic hosts was obtained by exploiting the inducing effect of the weakly coordinating tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB) anion that gives free "naked" cations. This method works very well with simple, conformationally mobile calix[6-7]arene ethers, which give conformationally blocked endo-calix or [2]pseudorotaxane complexes.

[graphs: see text] QM GIAO calculations of 13C and 1H chemical shift values of the ArCH2Ar group have been performed, using the hybrid DFT functional MPW1PW91 and the 6-31G(d,p) basis set, on some representative calixarenes and on a series of simplified calixarene models allowing derivation of chemical shift surfaces versus phi and chi dihedral angles. A good reproduction of experimental data was obtained. The applicability of chemical shift surfaces in the study of calixarene conformational features is illustrated.

Alkyl- and arylamidocalix[4]arene derivatives 1-11 have been designed and theoretically evaluated by docking studies as potential histone deacetylase inhibitors (HDACi). On the basis of the trimodal distribution of the calculated inhibition constants (K(i)), five alkyl- or arylamido derivatives (3, 7, 8, 9, and 11) were synthesized and tested. A qualitative accordance between the experimental results and the theoretical predictions was obtained, confirming that appropriately substituted arylamidocalix[4]arenes are active HDACi.

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