Thermodynamically Controlled, Dynamic Binding of Diols to a 1,2-BN Cyclohexane Derivative

Gregory P. Harlow, Lev N. Zakharov, Gang Wu, Shih-Yuan Liu
2013 Organometallics  
The reversible covalent binding of diols to an N-Bn 1,2-BN cyclohexane has been studied by 11B and 1H NMR spectroscopy and single-crystal X-ray diffraction analysis. The activation barrier for the reversible B-N Lewis acid-base interaction has been measured by variable-temperature NMR with bound (2R,3R)-(-)-2,3-butanediol (Tc = -40 °C, ΔG‡ = 11.2 ± 0.2 kcal mol-1). Deuterium labeling experiments demonstrate that ligand exchange is reversible and rapid at room temperature, and competitive
more » ... studies establish diol association as a thermodynamically controlled process.
doi:10.1021/om400697r pmid:25798022 pmcid:PMC4364440 fatcat:zmuu3rpxwfddvi5fv52tkpniaa