An insight on the aromatic changes in closed shell icosagen, tetrel, and pnictogen phenalenyl derivatives

Cristina Trujillo, Goar Sánchez-Sanz*, Ibon Alkorta, José Elguero

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A computational study of the aromatic and antiaromatic characteristics of closed shell charged phenalenyl (PLY+1 and PLY−1) upon replacement of the central carbon atom by icosagen (B, Al and Ga), tetrel (Si and Ge) and pnictogen (N, P and As) atoms comprising systems in which the icosagen and pnictogen derivatives considered are neutral while the tetrel ones are anions or cations, has been carried out at the B3LYP/6–311++G(d,p) computational level. By substitution, two different kinds of structures have been obtained, one planar (N and B) and another one bowl-shaped depending on the size of the central atom. In terms of aromaticity, the substitution of the central C atom causes a loss of the aromatic character in all cases as indicated by nucleus-independent chemical shifts (NICS) profiles and NICS values on the 0.001 au isosurface. Regarding the charge, PLY+1 presents larger electron delocalisation than PLY−1, phenomenon associated with aromaticity. Furthermore, the current density maps for those planar systems corroborate NICS findings, showing anticlockwise currents in PLY+1 (like in benzene) but clockwise in PLY-N0 and PLY-B0, indicating aromatic and antiaromatic behaviour, respectively.

Original languageEnglish
Pages (from-to)345-355
Number of pages11
JournalStructural Chemistry
Volume28
Issue number2
DOIs
Publication statusPublished - 1 Apr 2017

Keywords

  • Aromaticity
  • Icosagen
  • NICS
  • Phenalenyl
  • Pnictogen
  • Tetrel
  • Wiberg bond indices

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