Journal
CHEMICAL COMMUNICATIONS
Volume 56, Issue 26, Pages 3749-3752Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc00869a
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Funding
- National Institutes of Health NIGMS [R01-GM094541]
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A BN indole-containing aromatic scaffold has been synthesized and the cation-pi 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 (K-a'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-pi binding ability of the arene's pi-system with simple cations.
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