3D and 2D aromaticies: Like oil and water? The case of benzocarborane derivatives and 3D/3D fusions

23 March 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


2D/2D fusion of aromatic halves leading to a global aromatic is found in many polycyclic aromatic hydrocarbons. 3D/3D aromaticity is also found in fused boranes that follow the Jemmis’ mno rule, but 2D/3D aromaticity is difficult or impossible to achieve.


closo boranes
closo carboranes
Jemmis' mno rule

Supplementary materials

Supplementary information of "3D and 2D aromaticies: Like oil and water? The case of benzocarborane derivatives and 3D/3D fusions"
Table S1. NICS (in ppm) and MCI (in e) of rings of fused carborane and PAH system, and relative energies compared to the most stable isomer. Table S2. NICS and MCI of C2B10H12 and reference PAHs. Fig. S1. Bond lengths of the PAHs. Table S3. Cartesian coordinates of 3D/3D fused systems. Table S4. Cartesian coordinates of fused systems between carborane and PAHs. Table S5. Cartesian coordinates of reference aromatic systems. Table S6. Bond length alternation for the series of compounds under analysis. BLA has been computed as the longest and shortest bond lengths for each system. In the fused systems, no atom involved in the fusion between the two units has been considered. Only B-B bonds have been considered for the carboranes. Fig. S2 QTAIM data. QTAIM localization and delocalization indices of the 3D/3D systems formed from [Sn12]2- and [Sn10]2- clusters, and comparison to those for [B10H10]2-.


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