Investigation of 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one: Crystal structure, AIM and NBO analysis

Udayakumar, M.; Kothandapani, Jagatheeswaran; Ganesan, Subramaniapillai Selva; Venkataramanan, Natarajan Sathiyamoorthy; Kumar, Shankar; Byrappa, K.; Thamotharan, Subbiah

doi:10.1016/j.molstruc.2016.11.082

Cited by 25 publications

(8 citation statements)

References 27 publications

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“…This interaction is retained in the optimized structure with similar ρ and ∇ 2 ρ values. The above contact is also observed in the X-ray structure of IIA in addition to a short H2 [43][44][45][46] In the optimized structure of IIA, the pyridyl ring is slightly rotated to avoid this short…”

Section: Intramolecular Interactions In I and Iiamentioning

confidence: 90%

A quantitative study of weak noncovalent interactions in two pyridine isomers containing nitrile and thiophene moieties: a combined X-ray and theoretical investigation

et al. 2019

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Single crystals of two pyridine isomers containing cyano and thiophene moieties {systematic names: (Z)-2-(pyridine-2-yl)-3-(thiophen-2-yl)acrylonitrile, C 12 H 8 N 2 S, I and (Z)-2-(pyridine-3-yl)-3-(thiophen-2yl)acrylonitrile, C 12 H 8 N 2 S, II} were obtained from ethanol-cyclohexane mixture. The thiophene ring was found to be disordered over two orientations (syn and anti) in II. The potential energy surface scan of thiophene ring rotation suggests that the syn conformer is more stable by ≈ 4 kcal mol −1 than that of the anti-conformer. The optimized structures obtained using the DFT method (M06-2X/cc-pVTZ level of theory) show a high degree of similarity with the experimental structures. A detailed experimental and theoretical analysis on the intra-and intermolecular interactions observed in these structures is reported. The molecules arranged in the crystalline state are completely different in I and II. Intermolecular interactions are qualitatively analyzed using Hirshfeld surface and its associated 2D fingerprint plots. The intermolecular interaction energies of different molecular pairs are calculated using the PIXEL method. Several weak non-covalent interactions such as C-H • • •N, C-H • • • π, C-H • • •S, π • • • π and S • • • N contacts play a vital role in the stabilization of crystal structures. These interactions are further explored by the topological analysis of the electron density based on the quantum theory of the atoms-in-molecules approach.

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Section: Intramolecular Interactions In I and Iiamentioning

confidence: 90%

A quantitative study of weak noncovalent interactions in two pyridine isomers containing nitrile and thiophene moieties: a combined X-ray and theoretical investigation

et al. 2019

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“…63 The selection of M06-2X and basis set has been made on our earlier studies. [64][65][66][67][68][69] The vibrational frequency was calculated for the optimized geometry in vacuum and solvent phases to determine the energy minima on the potential energy surface and were found to have no negative frequencies. All the solution phase calculations were carried out by using the conductor-like polarizable continuum model (CPCM).…”

Section: Materials and Instrumentsmentioning

confidence: 99%

Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies

et al. 2019

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“…The DPI‐BA showed an absorption band in the range of 358–366 nm in different solvents, which can be attributed to the π‐ π* transition of the backbone. However, we observed an additional mild absorption band with λ max ∼302 nm in CHCl 3 , EtOH EtOAc and this mild band can be attributed to n‐π* transition . The absorption data in all solvents are summarized in Table .…”

Section: Resultsmentioning

confidence: 75%

¹H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis

et al. 2020

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In the present study the molecular structure of compound 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde [DPI‐BA] and its optoelectronic properties are reported. The SCXRD analysis revealed that DPI‐BA crystallizes in the Orthorhombic crystal system and Pca21 space group with Z=4. The intermolecular N‐H⋅⋅N interaction generates a one‐dimensional chain. An interesting halochromic behavior was observed for the DPI‐BA in THF:H2O (9:1) by varying the pH analysis. The fluorescence properties of neutral and acid‐base solutions were monitored by UV‐vis and 1D, 2D‐NMR studies. The HCl vapor was bubbled to the DPI‐BA in the DMSO‐d6 solution and the corresponding fluorescence wavelength changed from green (λem 501 nm) to blue (λem 459 nm). In the case of a basic pH solution was made by adding NaOH flakes to the DPI‐BA DMSO‐d6 solution and then the fluorescence wavelength changed from green to orange (λem 595 nm). The λmax of PL emission could be correlated to intermolecular charge transfer (ICT). The optical absorption and cyclic voltammetry measurement were performed to determine the bandgap. Besides, the quantitative analysis of intermolecular interactions through PIXEL, QTAIM, NBO, GIAO‐DFT methods and DFT studies was correlated to the experiments.

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Investigation of 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one: Crystal structure, AIM and NBO analysis

Cited by 25 publications

References 27 publications

A quantitative study of weak noncovalent interactions in two pyridine isomers containing nitrile and thiophene moieties: a combined X-ray and theoretical investigation

A quantitative study of weak noncovalent interactions in two pyridine isomers containing nitrile and thiophene moieties: a combined X-ray and theoretical investigation

Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies

¹H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis

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Investigation of 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one: Crystal structure, AIM and NBO analysis

Cited by 25 publications

References 27 publications

A quantitative study of weak noncovalent interactions in two pyridine isomers containing nitrile and thiophene moieties: a combined X-ray and theoretical investigation

A quantitative study of weak noncovalent interactions in two pyridine isomers containing nitrile and thiophene moieties: a combined X-ray and theoretical investigation

Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies

1H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis

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¹H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis