Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study
The electronic spectra of phenol, 2-chlorophenol, 2-aminophenol, and 2-nitrophenol have been studied both experimentally and computationally. The effect of the substituents on the solvatochromic behavior of the phenols were investigated in polar protic (methanol) and aprotic (dimethyl sulfoxide (DMS...
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| Format: | Article |
| Language: | English |
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Wiley
2018-01-01
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| Series: | Journal of Spectroscopy |
| Online Access: | http://dx.doi.org/10.1155/2018/4193657 |
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| author | Samuel Tetteh Ruphino Zugle John Prosper Kwaku Adotey Andrews Quashie |
| author_facet | Samuel Tetteh Ruphino Zugle John Prosper Kwaku Adotey Andrews Quashie |
| author_sort | Samuel Tetteh |
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| description | The electronic spectra of phenol, 2-chlorophenol, 2-aminophenol, and 2-nitrophenol have been studied both experimentally and computationally. The effect of the substituents on the solvatochromic behavior of the phenols were investigated in polar protic (methanol) and aprotic (dimethyl sulfoxide (DMSO)) solvents. The spectra of 2-nitrophenol recorded the highest red shift in methanol. The observed spectral changes were investigated computationally by means of density functional theory (DFT) methods. The gas phase compounds were fully optimized using B3LYP functionals with 6-31++G(d,p) bases set. The effects of the substituents on the electron distribution in the σ-bonds as well as the natural charge on the constituent atoms were analyzed by natural bond orbital (NBO) and natural population analysis (NPA). Second-order perturbation analyses also revealed substantial delocalization of nonbonding electrons on the substituents onto the phenyl ring, thereby increasing its electron density. Full interaction map (FIM) also showed regions of varying propensities for hydrogen and halogen bonding interactions on the phenols. |
| format | Article |
| id | doaj-art-483f971277364e1ca4dcfe7b679fd653 |
| institution | Kabale University |
| issn | 2314-4920 2314-4939 |
| language | English |
| publishDate | 2018-01-01 |
| publisher | Wiley |
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| series | Journal of Spectroscopy |
| spelling | doaj-art-483f971277364e1ca4dcfe7b679fd6532025-08-20T03:36:07ZengWileyJournal of Spectroscopy2314-49202314-49392018-01-01201810.1155/2018/41936574193657Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT StudySamuel Tetteh0Ruphino Zugle1John Prosper Kwaku Adotey2Andrews Quashie3Chemistry Department, School of Physical Sciences, College of Agriculture and Natural Sciences, University of Cape Coast, Cape Coast, GhanaChemistry Department, School of Physical Sciences, College of Agriculture and Natural Sciences, University of Cape Coast, Cape Coast, GhanaChemistry Department, School of Physical Sciences, College of Agriculture and Natural Sciences, University of Cape Coast, Cape Coast, GhanaInstitute of Industrial Research, Council for Scientific and Industrial Research, Cape Coast, GhanaThe electronic spectra of phenol, 2-chlorophenol, 2-aminophenol, and 2-nitrophenol have been studied both experimentally and computationally. The effect of the substituents on the solvatochromic behavior of the phenols were investigated in polar protic (methanol) and aprotic (dimethyl sulfoxide (DMSO)) solvents. The spectra of 2-nitrophenol recorded the highest red shift in methanol. The observed spectral changes were investigated computationally by means of density functional theory (DFT) methods. The gas phase compounds were fully optimized using B3LYP functionals with 6-31++G(d,p) bases set. The effects of the substituents on the electron distribution in the σ-bonds as well as the natural charge on the constituent atoms were analyzed by natural bond orbital (NBO) and natural population analysis (NPA). Second-order perturbation analyses also revealed substantial delocalization of nonbonding electrons on the substituents onto the phenyl ring, thereby increasing its electron density. Full interaction map (FIM) also showed regions of varying propensities for hydrogen and halogen bonding interactions on the phenols.http://dx.doi.org/10.1155/2018/4193657 |
| spellingShingle | Samuel Tetteh Ruphino Zugle John Prosper Kwaku Adotey Andrews Quashie Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study Journal of Spectroscopy |
| title | Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study |
| title_full | Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study |
| title_fullStr | Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study |
| title_full_unstemmed | Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study |
| title_short | Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study |
| title_sort | electronic spectra of ortho substituted phenols an experimental and dft study |
| url | http://dx.doi.org/10.1155/2018/4193657 |
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