Substituent effects on the gas-phase basicities of4-x-acetophanes and 4-x-2,6-dimethylacetophenones: a comparison with solution basicities

✍ Scribed by Carlo Dell'Erba; Angelo Mugnoli; Renato Noto; Marino Novi; Giorgio Occhiucci; Giovanni Petrillo; Fernando Sancassan; Domenico Spinelli

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 556 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01015-0

✦ Synopsis

Abstmct: The behaviour towards gas-phase protonation of a series of 2,6-dimethyl-4-X-acetophenones DMl exhibits strong similarities with that of the corresponding 4-X-acetophenones 1. A comparison with previous hasicity data in solution and AM1 semiempirical calculations suggest that the X-dependent rotation of the probe group out of the plane of the aromatic ring caused by the two orfho methyls is of minor importance in influencing the substituent effect on the gas-phase basic@ of DMl; on the contrary, it could heavily affect the solvatability and thus be responsible for the observed behaviour of DMl in strongly acidic media.