AAAA-DDDD Quadruple Hydrogen-Bond Arrays Featuring NH center dot center dot center dot N and CH center dot center dot center dot N Hydrogen Bonds
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The X-ray crystal structure of a previously reported extremely strong quadruple NH center dot center dot center dot N AAAA-DDDD hydrogen-bond array [5.4] (K-a 1.5 x 10(6) M-1 in CH3CN; K-a > 3 x 10(12) M-1 in CH2Cl2) features four short linear hydrogen bonds. Changing the two benzimidazole groups of the DDDD unit to triazole groups replaces two of the NH center dot center dot center dot N hydrogen bonds with CH center dot center dot center dot N interactions (complex [5.6]), but only reduces the association constant in CH3CN by 2 orders of magnitude (K-a = 2.6 x 10(4) M-1 in CH3CN; K-a > 1 x 10(7) M-1 in CH2Cl2). Related complexes without the triazole groups range in K-a from 18 to 270 M-1 in CH3CN, suggesting that the CH center dot center dot center dot N interactions can be considered part of a strong AAAA-DDDD quadruple hydrogen-bonding array. The NH center dot center dot center dot N/CH center dot center dot center dot N AAAA-DDDD motif can be repeatedly switched "on" and "off" in CDCl3 through successive additions of acid and base.
Leigh , D A , Robertson , C C , Slawin , A M Z & Thomson , P I T 2013 , ' AAAA-DDDD Quadruple Hydrogen-Bond Arrays Featuring NH center dot center dot center dot N and CH center dot center dot center dot N Hydrogen Bonds ' , Journal of the American Chemical Society , vol. 135 , no. 26 , pp. 9939-9943 . https://doi.org/10.1021/ja404504m
Journal of the American Chemical Society
© 2013. American Chemical Society. This is an article distributed in accordance with the terms of the Creative Commons Attribution (CC BY 4.0) International license, which permits others to distribute, remix, adapt and build upon this work, for noncommercial use, provided the original work is properly cited
DescriptionThis work is supported by funding from the EPSRC UK.
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