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Updated: Sep 24, 2025

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups
Published on: February 11, 2012
A computational study to determine whether substituents make E13[triple bond, length as m-dash]nitrogen (E13 = B, Al,
Shi-Lin Zhang1, Ming-Chung Yang1, Ming-Der Su1,2
1Department of Applied Chemistry, National Chiayi University Chiayi 60004 Taiwan midesu@mail.ncyu.edu.tw.
Abstract:
This study theoretically determines the effect of substituents on the stability of the triple-bonded L-E13[triple bond, length as m-dash]N-L (E13 = B, Al, Ga, In, and Tl) compound using the M06-2X/Def2-TZVP, B3PW91/Def2-TZVP, and B3LYP/LANL2DZ+dp levels of theory. Five small substituents (F, OH, H, CH3 and SiH3) and four large substituents (SiMe(SitBu3)2, SiiPrDis2, Tbt ([double bond, length as m-dash] C6H2-2,4,6-{CH(SiMe3)2}3) and Ar* ([double bond, length as m-dash]C6H3-2,6-(C6H2-2,4,6-i-Pr3)2)) are used. Unlike other triply bonded L-E13[triple bond, length as m-dash]P-L, L-E13[triple bond, length as m-dash]As-L, L-E13[triple bond, length as m-dash]Sb-L and L-E13[triple bond, length as m-dash]Bi-L molecules that have been studied, the theoretical findings for this study show that both small (but electropositive) ligands and bulky substituents can effectively stabilize the central E13[triple bond, length as m-dash]N triple bond. Nevertheless, these theoretical observations using the natural bond orbital and the natural resonance theory show that the central E13[triple bond, length as m-dash]N triple bond in these acetylene analogues must be weak, since these E13[triple bond, length as m-dash]N compounds with various ligands do not have a real triple bond.
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