Minimizing the Risk of Reporting False Aromaticity and Antiaromaticity in Inorganic Heterocycles Following Magnetic Criteria

• Published in: Inorganic chemistry Vol. 53; no. 7; pp. 3579 - 3585
• Main Authors: Torres-Vega, Juan J, Vásquez-Espinal, Alejandro, Caballero, Julio, Valenzuela, María L, Alvarez-Thon, Luis, Osorio, Edison, Tiznado, William
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 07.04.2014
• Subjects: Carbon Compounds, Inorganic - chemistry; Electromagnetic Fields; Heterocyclic Compounds - chemistry; Hydrocarbons, Aromatic - chemistry; Magnetic Phenomena; Quantum Theory
• ISSN: 0020-1669; 1520-510X; 1520-510X
• DOI: 10.1021/ic4030684

Although aromaticity is a concept in chemistry, in the last years, special efforts have been carried out in order to propose theoretical strategies to quantify it as a property of molecular rings. Among them, perhaps the computation of nucleus independent chemical shifts (NICSs) is the most commonly used, since it is possible to calculate it in an easy and fast way with most used quantum chemistry software. However, contradicting assignments of aromaticity by NICS and other methods have been reported in the literature, especially in studies concerning inorganic chemistry. In this Article is proposed a new and simple strategy to use the NICS information to assess aromaticity, identifying the point along the axis perpendicular to the molecular plane where the in-plane component of NICS becomes zero; it is called free of in-plane component NICS (FiPC-NICS). This spatial point is proposed as secure to consider NICS as an aromaticity descriptor; this simple proposal is evaluated in borazine and cyclotriphosphazenes. The results are compared with carefully examined aromatic stabilization energies and magnetically induced current-density analysis.