Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach
Three possible methyl-substituted phenyloxiranes have been synthesized in enantioenriched form (89-99% enantiomeric excess (ee)), and their vibrational absorption (VA) and vibrational circular dichroism (VCD)spectra have been recorded. The experimental spectra are compared to theoretical spectra obt...
| Main Authors: | , , , , , , |
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| Format: | Journal Article |
| Published: |
American Chemical Society
2006
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| Online Access: | http://pubs.acs.org/doi/abs/10.1021/jp060154m http://hdl.handle.net/20.500.11937/16397 |
| _version_ | 1848749165131071488 |
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| author | Fristrup, P. Lassen, P. Johannessen, C. Tanner, D. Norrby, P. Lars, H. Jalkanen, Karl |
| author_facet | Fristrup, P. Lassen, P. Johannessen, C. Tanner, D. Norrby, P. Lars, H. Jalkanen, Karl |
| author_sort | Fristrup, P. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | Three possible methyl-substituted phenyloxiranes have been synthesized in enantioenriched form (89-99% enantiomeric excess (ee)), and their vibrational absorption (VA) and vibrational circular dichroism (VCD)spectra have been recorded. The experimental spectra are compared to theoretical spectra obtained from quantum mechanical calculations (density functional theory with the B3LYP hybrid exchange correlation functional with 6-31++G**, aug-cc-pVDZ, or aug-cc-pVTZ basis set) and related to the physical structure of the compounds. The absolute configuration could be established directly in each case by comparing experimental and theoretical spectra. In addition, we have been able to document the changes that occur both in structures and in the VA and VCD spectra due to substituent effects on the oxirane ring. |
| first_indexed | 2025-11-14T07:16:36Z |
| format | Journal Article |
| id | curtin-20.500.11937-16397 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T07:16:36Z |
| publishDate | 2006 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-163972019-02-19T05:34:54Z Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach Fristrup, P. Lassen, P. Johannessen, C. Tanner, D. Norrby, P. Lars, H. Jalkanen, Karl Three possible methyl-substituted phenyloxiranes have been synthesized in enantioenriched form (89-99% enantiomeric excess (ee)), and their vibrational absorption (VA) and vibrational circular dichroism (VCD)spectra have been recorded. The experimental spectra are compared to theoretical spectra obtained from quantum mechanical calculations (density functional theory with the B3LYP hybrid exchange correlation functional with 6-31++G**, aug-cc-pVDZ, or aug-cc-pVTZ basis set) and related to the physical structure of the compounds. The absolute configuration could be established directly in each case by comparing experimental and theoretical spectra. In addition, we have been able to document the changes that occur both in structures and in the VA and VCD spectra due to substituent effects on the oxirane ring. 2006 Journal Article http://hdl.handle.net/20.500.11937/16397 10.1021/jp060154m http://pubs.acs.org/doi/abs/10.1021/jp060154m American Chemical Society restricted |
| spellingShingle | Fristrup, P. Lassen, P. Johannessen, C. Tanner, D. Norrby, P. Lars, H. Jalkanen, Karl Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach |
| title | Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach |
| title_full | Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach |
| title_fullStr | Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach |
| title_full_unstemmed | Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach |
| title_short | Direct Determination of Absolute Configuration of Methyl-Substituted Phenyloxiranes: Combined Experimental and Theoretical Approach |
| title_sort | direct determination of absolute configuration of methyl-substituted phenyloxiranes: combined experimental and theoretical approach |
| url | http://pubs.acs.org/doi/abs/10.1021/jp060154m http://hdl.handle.net/20.500.11937/16397 |