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Torsional Rotation in Ditopic Receptor Host and its Complex Formation with Resorcinol Guest: A Computational Study
Haobam Kisan Singh1, Manabendra Sarma1
1Department of Chemistry, Indian Institute of Technology Guwahati, Assam, 781039.
Abstract:
Noncovalent interactions due to the presence of heteroatoms in supramolecular compounds have gained a lot of attention. These different heteroatom-based supramolecular compounds have inspired us to examine the noncovalent interaction in the isolated host and host-guest complexes. In view of this, in the current manuscript, we investigated the stability and torsional energy barrier of different conformers of the ditopic receptor host 1,6-bis(2,6-bis(benzothiazol-2-yl) pyridine-4-yloxy) hexane (bbh). The conformer that is accompanied by intramolecular C-H⋯N and C-H⋯S interactions is relatively more stable than the others. Due to torsional angle rotation within the host, the C-H⋯N and C-H⋯S interactions get disrupted and exhibit different binding sites for capturing guest molecules. In addition, we have extended the investigation to understand the interaction energy and nature of interaction in host-guest (1 : 1 and 1 : 2) complexes formed between the host (bbh) and guest (resorcinol) by using different DFT functionals. Extended transition state-natural orbital chemical valence (ETS-NOCV) analysis of complexes revealed that the electrostatic interaction significantly contributes to the host-guest interaction energy. The noncovalent (NCI) analysis provides the existence of intermolecular hydrogen bonding and other weak interactions within the complexes.
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