Please use this identifier to cite or link to this item:
http://nopr.niscpr.res.in/handle/123456789/16312Full metadata record
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.author | Jeyaraman, R | - |
| dc.contributor.author | Thenmozhiyal, J C | - |
| dc.contributor.author | Murugadoss, R | - |
| dc.contributor.author | Venkatraj, M | - |
| dc.date.accessioned | 2013-03-09T10:49:56Z | - |
| dc.date.available | 2013-03-09T10:49:56Z | - |
| dc.date.issued | 1999-03 | - |
| dc.identifier.uri | http://hdl.handle.net/123456789/16312 | - |
| dc.description | 325-336 | en_US |
| dc.description.abstract | Ten N-formyl-cis-2,6-diarylpiperidines
have been prepared and their preferred conformations are determined using NMR spectral
studies and semiempirical calculations (AM1 and PM3 of MOPAC 6). The severe A 1,3 -strain due to the
interaction between the N-C=O group (coplanar to the C2-N1-C6 plane) and the
adjacent aryl group forces the N-forrnyl-cis-2,6- diarylpiperidines 19-28
to prefer
flattened boat conformations with nitrogen at one of the base positions (VIA
and VIB;
Figure1). Employing variable
temperature NMR studies, the barriers for N-C rotation in the N-formylpiperidin-4-one 19 and
the N-formylpiperidine 28 are found to be 72.5 and 65.8
kJ mol-1, respectively, which are in general, lower than those of the
corresponding N-nitrosopiperidines.
The lower energy barrier (ΔG#) of the N-formylpiperidine 28 compared to the N-formylpiperidin- 4-one 19 (by 6.7 kJ mol-l)
is attributed to the larger ground state destabilization of N- formylpiperidine 28
than 19. Semiempirical calculations
show a hydrogen bond type of attraction between the electron-rich oxygen atom
of N-C=O group and the electron deficient hydrogen at  -position (H2). | 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.38B(03) [March 1999] | en_US |
| dc.title | Influence of A 1,3 -strain on the conformational preferences and stereodynamics of N-formyl-cis-2,6-diarylpiperidines | en_US |
| dc.type | Article | en_US |
| Appears in Collections: | IJC-B Vol.38B(03) [March 1999] | |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 38B(3) 325-336.pdf | 2.31 MB | Adobe PDF | View/Open |
Items in NOPR are protected by copyright, with all rights reserved, unless otherwise indicated.