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| DC Field | Value | Language |
|---|---|---|
| dc.contributor.author | Vijayalakshmi, R | - |
| dc.contributor.author | Muthukumar, M | - |
| dc.contributor.author | Ponnuswamy, S | - |
| dc.contributor.author | Jeyaraman, R | - |
| dc.date.accessioned | 2012-08-06T07:37:03Z | - |
| dc.date.available | 2012-08-06T07:37:03Z | - |
| dc.date.issued | 2012-08 | - |
| dc.identifier.issn | 0975-0983(Online); 0376-4699(Print) | - |
| dc.identifier.uri | http://hdl.handle.net/123456789/14513 | - |
| dc.description | 1151-1162 | en_US |
| dc.description.abstract | The stereochemical consequences of the introduction of A1,3-strain by means of acetyl groups in r-2,c-6-diphenylpiperidin-4-one oximes have been studied using various NMR spectral techniques, X-ray crystallographic analysis and semiempirical MO calculations. The NMR spectral results show that the N,O-diacetylpiperidin-4-one oximes 12-15 prefer to adopt twist-boat conformation with an equilibrium between syn and anti rotamers. From the variable temperature 1H NMR spectral studies carried out on N,O-diacetyl-t-3-methyl-r-2,c-6-diphenylpiperidin-4-one oxime 13, the syn-anti rotational barriers DG#AB and DG#BA have been found to be 44.2 and 43.5 kJ mol-1, respectively. The X-ray crystal structure of N,O-diacetyl-t-3-isopropyl-r-2,c-6-diphenylpiperidin-4-one oxime 14 also show twist-boat conformation. The conformational preferences obtained from the semiempirical MO calculations for N,O-diacetylpiperidin-4-one oximes 12-15 have been found to be similar to those predicted from the NMR spectral studies and X-ray crystallographic analysis. Similarly, the N-acetyl-r-2,c-6-diphenylpiperidin-4-one oximes 5-7 have been found to adopt twist-boat conformations. | en_US |
| dc.language.iso | en_US | en_US |
| dc.publisher | NISCAIR-CSIR, India | en_US |
| dc.rights |  CC Attribution-Noncommercial-No Derivative Works 2.5 India | en_US |
| dc.source | IJC-B Vol.51B(08) [August 2012] | en_US |
| dc.subject | A1,3-strain | en_US |
| dc.subject | N-acetylpiperidin-4-one oximes | en_US |
| dc.subject | N,O-diacetylpiperidin-4-one oximes | en_US |
| dc.subject | NMR spectra | en_US |
| dc.subject | Semiempirical MO calculation | en_US |
| dc.subject | X-ray crystal structure | en_US |
| dc.subject | Variable temperature 1H NMR spectra | en_US |
| dc.title | Effect of A1,3-strain on the stereochemistry of N-acetyl and N,O-diacetyl-r-2,c-6-diphenylpiperidin-4-one oximes | en_US |
| dc.type | Article | en_US |
| Appears in Collections: | IJC-B Vol.51B(08) [August 2012] | |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 51B(8) 1151-1162.pdf | 114.42 kB | Adobe PDF | View/Open |
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