Ab initio molecular orbital calculations on acetyl cations. Relative hyperconjugative abilities of C-X bonds

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Abstract

Ab initio molecular orbital calculations have been carried out for the substituted acetyl cations RCO+ (R = CH3, CH3CH2, (CH3)2CH, (CH3)3C) and XCH2CO+ (X = CH3CH2, CH2=CH,CH=C, C=N, OH, F). The stabilities of the ions RCO+ are found to follow the normal inductive order of the substituents R. The calculations suggest that C-C hyper-conjugation is more effective than C-H hyper-conjugation.

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