title: Conjugation between σ- and π-Aromaticity in 1-C-Arylated Monocarba-closo-dodecaborate Anions.
abstract: Conjugation between σ- and π-aromatic moieties in 1-C-arylated monocarba-closo-dodecaborate anion derivatives 2 has been identified by means of kinetic experimental studies combined with theoretical calculations. We found that the reaction rate of iodination at the 12-B vertex of the carborane anion cage was affected by distal substituents on the benzene ring connected at the antipodal carbon vertex. Hammett and Yukawa-Tsuno plots indicated that substantial resonance effects are involved. Density functional theory calculations enabled detailed interpretation of the electronic interaction.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Mai
authors.initials: M
authors.lastname: Otsuka
authors.affiliation: RIKEN Center for Sustainable Resource Science , 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Ryo
authors.initials: R
authors.lastname: Takita
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Junichiro
authors.initials: J
authors.lastname: Kanazawa
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
authors.affiliation: RIKEN Center for Sustainable Resource Science , 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Atsuya
authors.initials: A
authors.lastname: Muranaka
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.|RIKEN Center for Sustainable Resource Science , 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Masanobu
authors.initials: M
authors.lastname: Uchiyama