Synthesis, characterization, thermal, X-ray, and DFT analyses
of 6-tert-butyl 3-ethyl 2-[(3-methoxy/5-bromo)-2-hydroxy
and (3-nitro/3-methoxy)benzylideneamino]-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate
- Received: June, 22, 2020
- Revised: July, 13, 2020
- Accepted for publication: July, 17, 2020
- DOI 10.26902/JSC_id68309
- Views: 195
1 Department of Chemistry, Faculty of Arts and Sciences, Hitit University, Corum, Turkey
2 Department of Physics, Faculty of Arts and Sciences, Hitit University, Corum, Turkey
3 Department of Food Processing, Technical Science Vocational School, Muş Alparslan University, Muş, Turkey
4 Department of Chemistry, Faculty of Arts and Sciences, Muş Alparslan University, Muş, Turkey
In this work, 6-tert-butyl 3-ethyl 2-amino-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate is synthesized from starting tert-butyl 4-oxopiperidine-1-carboxylate, ethyl cyanomalonate, and sulfur, and then, coupled with same aromatic aldehyde affords the corresponding Schiff base compounds. These compounds (2a—d) are characterized using FTIR, 1H and 13C NMR spectroscopic methods. The crystal and molecular structure of (E)-6-tert-butyl 3-ethyl 2-((2-hydroxy-3-methoxybenzylidene)amino)-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate (2a) is characterized by the X-ray crystallographic analysis. Compound 2a crystallizes in the monoclinic space group P21/c. The molecular and crystal structure is stabilized by two O—H⋯N and O—H⋯O intramolecular hydrogen bonds (O⋯N and O⋯O are 2.598(5) Å and 2.990(5) Å, respectively; O—H⋯N = 147° and O—H⋯O = 134°). According to DFT, compound 2d also shows the intramolecular hydrogen bonding, while there is no this type of interaction in compound 2b and 2c.
Keywords: heterocyclic amine, Schiff base, DFT, X-ray
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Импакт-фактор 2023 1.2 |
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Срок опубликования 4 мес |
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