Synthesis and Multinuclear Magnetic Resonance Study of Para-Substituted Phenyl Selenobenzoates

Article abstract of DOI:10.1021/jo00206a017

Eleven para-substituted Se-phenyl selenobenzoates, nine of which have not been previously reported, have been synthesized and characterized.The substituents include NO2, CN, C(O)CH3, C(O)OCH2CH3, F, Cl, Br, CH3, OCH3, and N(CH3)2.Selenium-77 and carbon-13 NMR chemical shifts and 77Se-13C spin-spin coupling constants have been obtained and assigned.Infrared carbonyl absorption frequencies were also determined.Selenium-77 chemical shifts ranged from 622.9 ppm for the dimethylamino-substituted compound to 650.4 ppm for the cyano-substituted compound.Single- and dual-substituent parameter analyses of the substituent chemical shifts for 77Se, C-1 of the phenyl ring, and the carbonyl carbon were performed.Single- and dual-substituent parameter analyses of the infrared carbonyl absorptions were done in conjunction with the above correlations.Although the 77Se chemical shift data did not give a good "fit", all other treatments gave an excellent fit.These results indicate that mesomeric substituents interact strongly with the aromatic ring and that the SeC(O)Ph moiety is electron deficient with respect to the substituted benzene.