Advertisement

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

Novel hydrogen bond observed between a carborane B–H and a phenyl ring

The ability to produce such interactions could prove useful for molecular assembly and pharmaceutical binding

by Jyllian Kemsley
March 7, 2016 | A version of this story appeared in Volume 94, Issue 10

[+]Enlarge
An iridium complex positions a carborane to form a B–H interaction with a phenyl group.
Structure of iridium complex with a boron hydrogen bond
An iridium complex positions a carborane to form a B–H interaction with a phenyl group.

A weak type of hydrogen bond is known to form between C–H, N–H, and O–H groups and the π electron cloud of an aromatic ring. Similar interactions have been predicted for B–H groups on compounds such as diborane (B2H6) and o-carborane (C2B10H12), in which the electronic structure produces a slight positive charge on the B–H hydrogens. A complex with a B–H···π interaction has now been created and characterized by a team led by Hong Yan of Nanjing University and Dieter Cremer of Southern Methodist University (J. Am. Chem. Soc. 2016, DOI: 10.1021/jacs.6b01249). The ability to promote such interactions could have applications in molecular assembly and pharmaceutical binding. The researchers treated an iridium-dithiolene-carborane complex with phosphines to produce a molecule in which a carborane B–H group is in position to form a hydrogen bond with one of the phosphine phenyl rings. The researchers confirmed the hydrogen bond experimentally using NMR and X-ray crystallography studies, finding a H···π distance of 240 to 276 pm. Computational analysis of the local stretching force constant of the hydrogen bond reveals that the strength of the B–H···π interaction is similar to that of the hydrogen bond in a water dimer.

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.