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Selenium‐77 NMR spectral analysis of selected substituted selenanes, selenanones and 3‐selena‐7‐azabicyclo[3.3.1]nonanes and derivatives
Author(s) -
Thompson M. Daniel,
Smith Gary S.,
Ramalingam K.,
Berlin K. Darrell
Publication year - 1986
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260241104
Subject(s) - chemistry , selenide , diselenide , substituent , selenium , spectral analysis , carbon 13 nmr , diphenyl diselenide , proton nmr , stereochemistry , computational chemistry , organic chemistry , spectroscopy , physics , quantum mechanics
A series of selenanes and selenanones have been examined using 77 Se NMR analysis. Sharp resonances were found in all cases whether recorded at 47.7, 51.4 or 57.22 MHz or in DCCI 3 or DMSO‐d 6 . Diphenyl diselenide was used as the external reference, but all resonances were subsequently referred to dimethyl selenide (0°C, O ppm). It was observed that in the selenanone family any substituent at the α‐, β‐ or γ‐positions exerted a significant effect on the 77 Se resonances. The same was true in the selenanes. Moreover, the presence of a chair‐chair or chair‐boat form in certain 3‐selena‐7‐azabicyclo[3.3.1]nonan‐9‐ones and related 3‐selena‐7‐azabicyclo[3.3.1]nonanes (and hydroperchlorates) induced remarkable differences in 77 Se shifts. Some general observations and conclusions are delineated in terms of the influence of various groups on the 77 Se resonances in these cyclic systems.