B-H···π Interaction: A New Type of Nonclassical Hydrogen Bonding

Journal of the American Chemical Society
Xiaolei ZhangDieter Cremer

Abstract

For the first time, nonclassical hydrogen (H)-bonding involving a B-H···π interaction is described utilizing both quantum chemical predictions and experimental realization. In the gas phase, a B-H···π H-bond is observed in either B2H6···benzene (ΔE = -5.07 kcal/mol) or carborane···benzene (ΔE = -3.94 kcal/mol) complex at reduced temperatures. Ir-dimercapto-carborane complexes [Cp*Ir(S2C2B10H10)] are designed to react with phosphines PR3 (R = C6H4X, X = H, F, OMe) to give [Cp*Ir(PR3)S2C2B10H10] for an investigation of B-H···π interactions at ambient temperatures. X-ray diffraction studies reveal that the interaction between the carborane BH bonds and the phosphine aryl substituents involves a BH···π H-bond (H···π distance: 2.40-2.76 Å). (1)H NMR experiments reveal that B-H···π interactions exist in solution according to measured (1)H{(11)B} signals at ambient temperatures in the range 0.0 ≤ δ ≤ 0.3 ppm. These are high-field shifted by more than 1.5 ppm relative to the (1)H{(11)B} signals obtained for the PMe3 analog without B-H···π bonding. Quantum chemical calculations suggest that the interaction is electrostatic and the local (B)H···ring stretching force constant is as large as the H-bond stretching force constant in the wate...Continue Reading

References

Mar 20, 2003·Angewandte Chemie·Emmanuel A MeyerFrançois Diederich
Dec 26, 2003·Chemistry : a European Journal·Colin L Raston, Gareth W V Cave
Nov 29, 2005·Angewandte Chemie·Juan C LópezJosé L Alonso
Apr 20, 2006·Journal of the American Chemical Society·Sascha VaupelKwang S Kim
May 4, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Jindrich FanfrlíkPavel Hobza
Aug 14, 1992·Science·S SuzukiG A Blake
Mar 5, 2008·The Journal of Chemical Physics·Jeng-Da Chai, Martin Head-Gordon
Nov 8, 2008·Physical Chemistry Chemical Physics : PCCP·Jeng-Da Chai, Martin Head-Gordon
Apr 2, 2009·The Journal of Chemical Physics·Jürgen Gräfenstein, Dieter Cremer
Feb 15, 2011·Asian Journal of Andrology·Sidney R Grimes
Jul 3, 2013·Physical Chemistry Chemical Physics : PCCP·Laura E Ratcliff, Peter D Haynes
Aug 10, 2013·The Journal of Physical Chemistry. a·Robert KalesckyDieter Cremer
Dec 7, 2013·The Journal of Physical Chemistry. a·Robert KalesckyDieter Cremer

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Citations

Jul 8, 2016·Journal of the American Chemical Society·Rafal M DziedzicAlexander M Spokoyny
Dec 15, 2016·Inorganic Chemistry·Vytor OliveiraDieter Cremer
Mar 7, 2017·Chemistry : a European Journal·Christoph SelgKirsten Zeitler
May 31, 2017·Physical Chemistry Chemical Physics : PCCP·Jindřich FanfrlíkPavel Hobza
Feb 21, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Xiancui ZhuShuangliu Zhou
Oct 11, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·M LoorS Schulz
Oct 7, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ankit SinghHimansu S Biswal
Aug 25, 2018·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Rahul ShuklaDeepak Chopra
Sep 13, 2018·Physical Chemistry Chemical Physics : PCCP·Dani SetiawanElfi Kraka
Oct 5, 2018·Journal of Computational Chemistry·Changwei WangYirong Mo
Feb 7, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Ronglin PangXu-Qiong Xiao
May 8, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Daniel SethioElfi Kraka
Sep 3, 2019·Physical Chemistry Chemical Physics : PCCP·Antonio Frontera, Antonio Bauzá
Sep 28, 2017·Journal of Computational Chemistry·Changwei WangYirong Mo
Sep 29, 2020·Journal of Molecular Modeling·Yunwen TaoElfi Kraka
Feb 1, 2019·Journal of Molecular Modeling·Niraj VermaElfi Kraka
Sep 6, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lei GanJosé G Planas
Sep 21, 2016·Chemistry : a European Journal·Jörg Grunenberg
Oct 28, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniel SethioElfi Kraka
Dec 22, 2019·Materials·Vytor P OliveiraElfi Kraka
Aug 2, 2020·Chemistry : a European Journal·Marcos CoutoHugo Cerecetto
Mar 6, 2021·The Journal of Physical Chemistry. B·Niraj VermaElfi Kraka
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nassim BeiranvandElfi Kraka
May 4, 2021·Wiley Interdisciplinary Reviews. Computational Molecular Science·Lucas J KarasJudy I-Chia Wu
Nov 21, 2017·The Journal of Physical Chemistry. a·Vytor Oliveira, Elfi Kraka
Dec 5, 2020·ACS Central Science·Jia-Hong HuangThomas C W Mak
Aug 8, 2017·The Journal of Physical Chemistry. a·Vytor OliveiraElfi Kraka
Sep 21, 2017·Organic Letters·Chun-Xiao LiChang-Sheng Lu
Nov 23, 2019·Journal of the American Chemical Society·Yizhen YinHiroaki Suga
Nov 17, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Roberto Fernandez-AlvarezPavel Matějíček
Aug 7, 2017·Journal of the American Chemical Society·Xiaolei ZhangHong Yan
Jul 20, 2019·The Journal of Physical Chemistry. a·Siying LyuElfi Kraka
Oct 29, 2021·Inorganic Chemistry·Bennett J EleazerDmitry V Peryshkov
Nov 25, 2021·The Journal of Physical Chemistry. a·Li ChenYirong Mo

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