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

Organometallics
Gregory P HarlowShih-Yuan Liu

Abstract

The reversible covalent binding of diols to an N-Bn 1,2-BN cyclohexane has been studied by (11)B and (1)H 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 (T c = -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 binding studies establish diol association as a thermodynamically controlled process.

References

Aug 1, 1984·Journal of Medicinal Chemistry·M A GrassbergerJ Hildebrandt
Mar 20, 2003·Angewandte Chemie·David J H EmslieMasood Parvez
Dec 16, 2003·Angewandte Chemie·Jeff T SuriBakthan Singaram
Oct 8, 2004·Organic Letters·Kristen E Secor, Timothy E Glass
Feb 22, 2005·Current Opinion in Biotechnology·Ramachandram BaduguChris D Geddes
May 12, 2005·Chemical Reviews·Michael E Jung, Grazia Piizzi
Jan 26, 2006·Journal of the American Chemical Society·Lei ZhuEric V Anslyn
Mar 30, 2006·Journal of the American Chemical Society·Meenakshi Dowlut, Dennis G Hall
Aug 17, 2006·Journal of the American Chemical Society·Cory A JaskaMasood Parvez
Feb 1, 2007·Journal of the American Chemical Society·Soya GamseyBakthan Singaram
Mar 7, 2007·Organic Letters·Michael J D BosdetMasood Parvez
Apr 6, 2007·Angewandte Chemie·Michael J D BosdetMasood Parvez
Jul 27, 2007·Angewandte Chemie·Alexander SchillerBakthan Singaram
Oct 20, 2007·Organic Letters·Adam J V MarwitzShih-Yuan Liu
Nov 15, 2007·Angewandte Chemie·Zhiqiang Liu, Todd B Marder
Aug 15, 2008·Journal of the American Chemical Society·Akio OjidaItaru Hamachi
Dec 24, 2008·Angewandte Chemie·Adam J V MarwitzShih-Yuan Liu
Jan 21, 2010·Chemical Communications : Chem Comm·Adam J V MarwitzShih-Yuan Liu
Aug 24, 2010·Chemical Communications : Chem Comm·Marc LepeltierDmitrii F Perepichka
Sep 8, 2010·Angewandte Chemie·Adam J V MarwitzShih-Yuan Liu
Dec 15, 2010·Journal of the American Chemical Society·Patrick G CampbellShih-Yuan Liu
Jul 14, 2011·Angewandte Chemie·Ashley N LammShih-Yuan Liu
Jul 27, 2011·Journal of the American Chemical Society·Wei LuoShih-Yuan Liu
Oct 27, 2011·Journal of the American Chemical Society·Takuji HatakeyamaMasaharu Nakamura
Jan 31, 2012·The Journal of Organic Chemistry·John W Tomsho, Stephen J Benkovic
May 31, 2012·Angewandte Chemie·Patrick G CampbellShih-Yuan Liu
Aug 21, 2012·The Journal of Organic Chemistry·Rebecca BraslauMariEllen Cottman
Nov 22, 2012·Journal of the American Chemical Society·Takuji HatakeyamaMasaharu Nakamura
Feb 21, 2013·Chemical Communications : Chem Comm·Cam Thuy HoangTiffany R Walsh
Apr 9, 2013·Angewandte Chemie·Jia-Sheng LuSuning Wang
Jul 9, 2013·Angewandte Chemie·Gabriel E RudebuschShih-Yuan Liu

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