Activation of a carbonyl compound by halogen bonding.
作者： Stefan H. Jungbauer , Sebastian M. Walter , Severin Schindler , Laxmidhar Rout , Florian Kniep
DOI: 10.1039/C4CC03124E
关键词:
摘要: Using a prototypical Diels–Alder reaction as benchmark, we show that dicationic halogen-bond donors are capable of activating neutral organic substrate. By various comparison experiments, the action traces acid or other structural features donor not related to halogen bonding excluded with high certainty.
rsc.org
core.ac.uk
sci-hub.se 参考文章(38)
Abigail G. Doyle, Eric N. Jacobsen, Small-molecule H-bond donors in asymmetric catalysis. Chemical Reviews. ,vol. 107, pp. 5713- 5743 ,(2007) , 10.1021/CR068373R
O. Hassel, Chr. Rømming, Direct structural evidence for weak charge-transfer bonds in solids containing chemically saturated molecules Q. Rev. Chem. Soc.. ,vol. 16, pp. 1- 18 ,(1962) , 10.1039/QR9621600001
Yunxiang Lu, Yong Wang, Weiliang Zhu, Nonbonding interactions of organic halogens in biological systems: implications for drug discovery and biomolecular design Physical Chemistry Chemical Physics. ,vol. 12, pp. 4543- 4551 ,(2010) , 10.1039/B926326H
Nathan L. Kilah, Matthew D. Wise, Christopher J. Serpell, Amber L. Thompson, Nicholas G. White, Kirsten E. Christensen, Paul D. Beer, Enhancement of anion recognition exhibited by a halogen-bonding rotaxane host system. Journal of the American Chemical Society. ,vol. 132, pp. 11893- 11895 ,(2010) , 10.1021/JA105263Q
Sebastian M. Walter, Florian Kniep, Eberhardt Herdtweck, Stefan M. Huber, Halogen‐Bond‐Induced Activation of a Carbon–Heteroatom Bond Angewandte Chemie. ,vol. 50, pp. 7187- 7191 ,(2011) , 10.1002/ANIE.201101672
Florian Weigend, Reinhart Ahlrichs, Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Physical Chemistry Chemical Physics. ,vol. 7, pp. 3297- 3305 ,(2005) , 10.1039/B508541A
Kirk A. Peterson, Detlev Figgen, Erich Goll, Hermann Stoll, Michael Dolg, Systematically convergent basis sets with relativistic pseudopotentials. II. Small-core pseudopotentials and correlation consistent basis sets for the post-d group 16–18 elements The Journal of Chemical Physics. ,vol. 119, pp. 11113- 11123 ,(2003) , 10.1063/1.1622924
Zhiguo Zhang, Peter R. Schreiner, (Thio)urea organocatalysis—What can be learnt from anion recognition? Chemical Society Reviews. ,vol. 38, pp. 1187- 1198 ,(2009) , 10.1039/B801793J
Pierangelo Metrangolo, Franck Meyer, Tullio Pilati, Giuseppe Resnati, Giancarlo Terraneo, Halogen Bonding in Supramolecular Chemistry Angewandte Chemie. ,vol. 47, pp. 6114- 6127 ,(2008) , 10.1002/ANIE.200800128
Sebastian M. Walter, Florian Kniep, Laxmidhar Rout, Franz P. Schmidtchen, Eberhardt Herdtweck, Stefan M. Huber, Isothermal Calorimetric Titrations on Charge-Assisted Halogen Bonds: Role of Entropy, Counterions, Solvent, and Temperature Journal of the American Chemical Society. ,vol. 134, pp. 8507- 8512 ,(2012) , 10.1021/JA2119207