Stereoselective green synthesis and molecular structures of highly functionalized spirooxindole-pyrrolidine hybrids – A combined experimental and theoretical investigation
| Autor: | Natarajan Arumugam, Saied M. Soliman, Hazem A. Ghabbour, Mohammad Altaf, Raju Suresh Kumar, Bellie Sundaram Krishnamoorthy, Raju Ranjith Kumar, Abdulrahman I. Almansour |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemical shift Organic Chemistry Nuclear magnetic resonance spectroscopy Carbon-13 NMR 010402 general chemistry 01 natural sciences Pyrrolidine Cycloaddition 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Computational chemistry Molecule Density functional theory Spectroscopy Natural bond orbital |
| Zdroj: | Journal of Molecular Structure. 1152:266-275 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2017.09.073 |
| Popis: | Highly functionalized spirooxindole-pyrrolidine hybrids have been synthesized stereoselectively through a [3 + 2] cycloaddition strategy in an ionic liquid, 1-butyl-3-methylimidazolium bromide ([bmim]Br). The structure of these spiro heterocyclic hybrids was elucidated using one and two dimensional NMR spectroscopy, single crystal X-ray crystallographic studies and Density Functional Theory (DFT) calculations. The calculated geometric parameters are in good agreement with the experimental data obtained from the X-ray structures. The Natural Bond Orbital (NBO) calculations on these molecules confirm the electron rich carbonyl oxygen and electron deficient NH groups. The 1H and 13C NMR chemical shifts calculated using GIAO method are in good agreement with the experimental data. The DFT computed polarizability values also suggest the possible NLO activity of these molecules. |
| Databáze: | OpenAIRE |
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