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Synthesis, characterization of two new bicyclic oxazolidines and investigation of their optoelectronic properties using density functional theory

Authors:

Ghulam Abbas,

Karlsruhe Institute of Technology, DE
About Ghulam
Institut für Anorganische Chemie
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Ahmad Irfan ,

King Khalid University, SA
About Ahmad
Research Center for Advanced Materials Science (RCAMS)
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Shahid Hameed,

Quaid-i-Azam University, PK
About Shahid
Department of Chemistry
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Abdullah G. Al-Sehemi,

King Khalid University, SA
About Abdullah G.
Research Center for Advanced Materials Science (RCAMS)
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Ruifa Jin,

Chifeng University, CN
About Ruifa
College of Chemistry and Chemical Engineering
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Shanshan Tang

Jilin Agriculture University, CN
About Shanshan
College of Life Science
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Abstract

This paper presents a facile synthetic route to synthesise two new bicyclic oxazolidine compounds 3,5-bis(4- chlorophenyl)-7a-methyldihydro-1H-[1,3]oxazolo[3,4-c][1,3] oxazole (1) and 3,5-bis(2-methoxyphenyl)-7a-methyldihydro- 1H-[1,3]oxazolo[3,4-c][1,3]oxazole (2). The condensation reaction between 2-amino-2-methylpropane-1, 3-diol (ampdH2) and choloro- and methoxy- substituted aromatic aldehyde yielded the heterocyclic bicyclic compounds (1) and (2), respectively. The compounds are characterised by FT-IR and 1HNMR spectroscopy and structures are conclusively determined by single crystal X-ray diffraction analysis. The ground state geometries are optimised by using density functional theory (DFT) at B3LYP/6-31G** level of theory to compare the geometric parameters (bond lengths, bond angles and torsion angles) with the X-ray crystallographic data. The computed geometric parameters are in good agreement with the experimental data. To shed light on the electronic and photophysical properties, DFT/B3LYP/6-31G** and time dependent DFT have been applied, respectively. Intra-molecular charge transfer has been observed in both the compounds. The absorption wavelengths are calculated with and without the solvent (acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide and methanol) at TD-B3LYP/6-31G** level of theory.

How to Cite: Abbas, G. et al., (2018). Synthesis, characterization of two new bicyclic oxazolidines and investigation of their optoelectronic properties using density functional theory. Journal of the National Science Foundation of Sri Lanka. 46(2), pp.197–204. DOI: http://doi.org/10.4038/jnsfsr.v46i2.8420
Published on 30 Jun 2018.
Peer Reviewed

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