Katherine Boknevitz1, Clovis Darrigan2, Anna Chrostowska2, Shih-Yuan Liu3. 1. Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467, USA. shihyuan.liu@bc.edu. 2. Universite de Pau et des Pays de l'Adour, E2S UPPA, CNRS, IPREM, Pau, France. 3. Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467, USA. shihyuan.liu@bc.edu and Universite de Pau et des Pays de l'Adour, E2S UPPA, CNRS, IPREM, Pau, France.
Abstract
A BN indole-containing aromatic scaffold has been synthesized and the cation-π binding ability characterized by nuclear magnetic resonance (NMR) monitored titrations. The resulting chemical shifts were analyzed using a non-linear curve fitting procedure and the extracted association constants (Ka's) compared with the natural indole scaffold. Computations were also performed to support our findings. This work shows that incorporation of a B-N bond in place of a C-C bond in an aromatic system slightly lowers the cation-π binding ability of the arene's π-system with simple cations.
A BN indole-containing aromatic scaffold has been synthesized and the cation-π binding ability characterized by nuclear magnetic resonance (n class="Chemical">NMR) monitored titrations. The resulting chemical shifts were analyzed using a non-linear curve fitting procedure and the extracted association constants (Ka's) compared with the natural indole scaffold. Computations were also performed to support our findings. This work shows that incorporation of a B-N bond in place of a C-C bond in an aromatic system slightly lowers the cation-π binding ability of the arene's π-system with simple cations.
Authors: Ayan Bhattacharjee; Geraint H M Davies; Borna Saeednia; Steven R Wisniewski; Gary A Molander Journal: Adv Synth Catal Date: 2020-12-23 Impact factor: 5.837