Polar substituent effects in the bicyclo[1.1.1]pentane ring system: Acidities of 3-substituted bicyclo[1.1.1]pentane-1-carboxylic acids
W Adcock, Y Baran, A Filippi, M Speranza, NA Trout
article (Uluslararası, Hakemli) | Yazar(lar): W Adcock, Y Baran, A Filippi, M Speranza, NA Trout | Yıl: 2005 | Dergi/Kurum: JOURNAL OF ORGANIC CHEMISTRY | İndeks: WOS.SCI,WOS.IC | DOI: 10.1021/jo040236b — Özet: Experimental gas-phase acidities are reported for a series of 3-substituted (X) bicyclo [1.1.1]pent-1-yl carb
Experimental gas-phase acidities are reported for a series of 3-substituted (X) bicyclo [1.1.1]pent-1-yl carboxylic acids (1, Y = COOH). A comparison with available calculated data (MP2/6-311++G**//B3LYP/6-311+G**) reveals good agreement. The relative substituent effects are shown to be adequately described by a much lower level of theory (B3LYP/6-31+G*). Various correlations are presented which clearly point to polar field effects as being the origin of the relative acidities.