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- W843989413 abstract "Ab initio calculations are carried out on protonation equilibria of 5-memberedheteroaromatic aldehydes (5MHAs;heteroatom Y = NH, O, PH,and S and substituentZ = NH2, OCH3, SCH3, CH3, H, Cl, CHO, CN,NO2) at the level. Naturalbond orbital (NBO) analyses show that the optimal localized natural Lewis structures of the protonated aldehydes,(P), are ortho (C3) protonated (for Y = O, PH and S) and N-pro-tonated (for Y = NH) forms in contrast to the standard structural Lewis formula for aldehydes, (R). The delo-calizability of the heteroatom is in the order Y = NH > O > S > PH. The transmission efficiency of (Z) substituent effects to the carbonyl moiety run parallel to the delocalizability of for R,but is dominantly influenced by the cationic charge on for P, which is in the reverse order of thede-localizability of The Hammett for variation of Z in the protonation are determined by the dif-ference in the transmission efficiencies between Pand R stateat simple interpretation of their magnitude is not warranted. However,the magnitude of the gas-phase values decreases as the level ofcomputation is raised from RHF/3-21G* to RHF/6-31G* and to but increases again at the MP4SDQ/6-31G* level. Further decrease occurs when solvent effect (water) is accounted for by the SCRF method. Comparison of the SCRF with those determined in the aqueous acid solution for Y = S and CHCH shows inadequacy of accounting for the solvent effects on the by a continuum model. It is noteworthy that semiempirical calculations, especially theAM1 method, give even lower magnitude of the gas-phase" @default.
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- W843989413 date "2000-09-01" @default.
- W843989413 modified "2023-09-24" @default.
- W843989413 title "Transmission of Substituent Effects through 5-Membered Heteroaromatic Rings" @default.
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