Correlating Solution- and Solid-State Structures of Conformationally Flexible Resorcinarenes: Significance of a Sulfonyl Group in Intramolecular Self-Inclusion.

ABSTRACT: The synthesis of tetramethoxyresorcinarene podands bearing p-toluene arms connected by -SO3 - (1) and -CH2 O- (2) linkers is presented herein. In the solid state, the resorcinarene podand 1 forms an intramolecular self-inclusion complex with the pendant p-toluene group of a podand arm, whereas the resorcinarene podand 2 does not show self-inclusion. The conformations of the flexible resorcinarene podands in solution were investigated by variable-temperature experiments using 1D and 2D NMR spectroscopic techniques as well as by computational methods, including a conformational search and subsequent DFT optimisation of representative structures. The 1 H NMR spectra of 1 and 2 at room temperature show a single set of proton signals that are in agreement with C4v symmetry. At low temperatures,

SUBMITTER: Pamula M 

PROVIDER: S-EPMC7317440 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature