Exploring Chimeric Calix[4]tetrolarene Molecular Scaffolds: Theoretical Investigations
| Autor: | Shridhar P. Gejji, Dipali N. Lande |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Chemistry
02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Potential energy 0104 chemical sciences Crystallography Cone (topology) Calixarene Density functional theory Physical and Theoretical Chemistry Energy structure Solubility 0210 nano-technology Conformational isomerism |
| Zdroj: | The Journal of Physical Chemistry A. 122:4189-4197 |
| ISSN: | 1520-5215 1089-5639 |
| DOI: | 10.1021/acs.jpca.8b01686 |
| Popis: | The structure and spectral characteristics of the chimeric mixture of calixarene and pyrogallolarene (usually referred to as calix[4]tetrolarene) and its derivatives are studied employing the M06-2X-based density functional theory. Different conformers, viz., cone, partial cone, 1,2-alternate, and 1,3-alternate, were identified as the stationary point structures on their potential energy surfaces. Among these, the symmetric C4v cone conformer is found to be energetically favorable, which can be attributed to the cyclic array of hydrogen-bonding network in the calix[4]tetrolarene or its thia analogue. The substitution of methoxy groups at the upper rims of calix[4]tetrol- and thicalix[4]tetrol-arenes significantly influences the cooperative hydrogen-bonding network and conformational behavior of these hosts. The methoxy-substituted macrocycles show lowering in symmetry from C4v to C2v, engendering the pinched cone conformer to be the lowest energy structure. The enhanced solubility of the modified calix[4]... |
| Databáze: | OpenAIRE |
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