Structure and absolute configuration of some 5-chloro-2-methoxy-N-phenylbenzamide derivatives
| Autor: | ElSayed M. Shalaby, Atef G Hanna, A. Abouelsayed, Medhat Ibrahim, Emad A. Al-Ashkar, Alaaeldin M. F. Galal |
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| Rok vydání: | 2018 |
| Předmět: |
Stereochemistry
Molecular Conformation 02 engineering and technology Crystallography X-Ray 010402 general chemistry Ring (chemistry) 01 natural sciences Analytical Chemistry chemistry.chemical_compound Amide Spectroscopy Fourier Transform Infrared Moiety Molecule Reactivity (chemistry) Instrumentation Spectroscopy Chemistry Absolute configuration Hydrogen Bonding 021001 nanoscience & nanotechnology Atomic and Molecular Physics and Optics 0104 chemical sciences Crystallography Benzamides Spectrophotometry Ultraviolet Density functional theory 0210 nano-technology Single crystal |
| Zdroj: | Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 188:213-221 |
| ISSN: | 1386-1425 |
| DOI: | 10.1016/j.saa.2017.06.068 |
| Popis: | The absolute configuration of 5-chloro-2-methoxy-N-phenylbenzamide single crystal [compound (1)] and the effect of introducing -[CH2]n-, n=1,2 group adjacent to the amide group [compounds (2) and (3)], were studied. Furthermore, the replacement of the methoxy group with a hydroxy group [compound (4)] was defined. Proton and carbon-13 NMR spectrometer were used to record the structural information of the prepared compounds. X-ray single crystal diffractometer were used to elucidate the 3D structural configurations. Intensity data for the studied compounds were collected at room temperature. The X-ray data prove that compound (1) is almost planar, with maximum r.m.s. deviations of 0.210(3)A corresponds to C13. This planarity starts to disturb by adding -[CH2]n-, n=1,2 groups between the NH group and the phenyl ring in compounds (2) and (3), respectively. By replacing the OCH3 group by an OH group in compound (4), the plane of the chlorophenyl moiety is nearly perpendicular to that of the phenyl ring. Such new structural configurations were further illustrated by the infrared, and ultraviolet-visible spectroscopy measurements in the frequency range 400-4000cm-1 and 190-1100nm, respectively. Spectroscopic analyses were verified with the help of molecular modeling using density functional theory. The estimated total dipole moment for the prepared compounds reflects its ability to interact with its surrounding molecules. The higher dipole moment for a given structures is combined with the higher reactivity for potential use in medicinal applications. |
| Databáze: | OpenAIRE |
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