title: Polar substituent effects in the bicyclo[1.1.1]pentane ring system: acidities of 3-substituted bicyclo[1.1.1]pentane-1-carboxylic acids.
abstract: 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.
authors.affiliation: School of Chemistry, Physics, and Earth Sciences, The Flinders University of South Australia, Adelaide, Australia 5001. william.adcock@flinders.edu.au
authors.forename: William
authors.initials: W
authors.lastname: Adcock
authors.forename: Yakup
authors.initials: Y
authors.lastname: Baran
authors.forename: Antonello
authors.initials: A
authors.lastname: Filippi
authors.forename: Maurizio
authors.initials: M
authors.lastname: Speranza
authors.forename: Neil A
authors.initials: NA
authors.lastname: Trout