Document Type


Journal/Book Title

International Journal of Quantum Chemistry

Publication Date




First Page


Last Page



The carbene triel bond is predicted and characterized by theoretical calculations. The C lone pair of N‐heterocyclic carbenes (NHCs) is allowed to interact with the central triel atom of TrR3 (Tr = B and Al; R = H, F, Cl, and Br). The ensuing bond is very strong, with an interaction energy of nearly 90 kcal/mol. Replacement of the C lone pair by that of either N or Si weakens the binding. The bond is strengthened by electron‐withdrawing substituents on the triel atom, and the reverse occurs with substitution on the NHC. However, these effects do not strictly follow the typical pattern of F > Cl > Br. The TrR3 molecule suffers a good deal of geometric deformation, requiring on the order of 30 kcal/mol, in forming the complex. The R(C···Tr) bond is quite short, for example, 1.6 Å for Tr = B, and shows other indications of at least a partially covalent bond, such as a high electron density at the bond critical point and a good deal of intermolecular charge transfer.


This is the peer reviewed version of the following article: Chi Z, Dong W, Li Q, Yang X, Scheiner S, Liu S. Carbene triel bonds between TrR3 (Tr = B, Al) and N‐heterocyclic carbenes. Int J Quantum Chem. 2018;e25867., which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.



To view the content in your browser, please download Adobe Reader or, alternately,
you may Download the file to your hard drive.

NOTE: The latest versions of Adobe Reader do not support viewing PDF files within Firefox on Mac OS and if you are using a modern (Intel) Mac, there is no official plugin for viewing PDF files within the browser window.