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Aromatic character of fluorinated pyridines

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Abstract

Geometric structures for all the possible isomers of fluorinated pyridines were optimized at the B3LYP/6-311++G(d,p) level of theory. Aromaticities of the considered molecules were investigated using different indices included geometry-based (HOMA and Bird [I 6]), magnetism-based (NICS(1) and diamagnetic susceptibility anisotropy [Δχ]), π- and σ-electron count-based (pEDA, sEDA), and recently introduced electronic-based (electric field gradient [EFG(0), EFG(0.5)] and Shannon aromaticity) indices. Moreover, we used also HOMO–LUMO gap, atomization energy (D 0), and interaction energy for fluorinated pyridine complexes by water molecule as global descriptors, and the EFG values (EFGC–F(0)) on the middle points of C–F bonds and σ-electron population (N σ) of nitrogen atom as local descriptors. All studied indices except HOMA and EFG(0.5) are well correlated to each other and to global and local descriptors.

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Acknowledgments

We would like to thank Dr. Fatih Ucun from Department of Physics (Süleyman Demirel University) in Isparta (Turkey) for helpful discussions about the aromaticity calculations.

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Authors and Affiliations

  1. Department of Physics, Faculty of Arts and Sciences, Süleyman Demirel University, 32260, Isparta, Turkey

    Ahmet Tokatlı & Salih Akyürekli

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  1. Ahmet Tokatlı
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  2. Salih Akyürekli
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Correspondence to Ahmet Tokatlı.

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Tokatlı, A., Akyürekli, S. Aromatic character of fluorinated pyridines. Struct Chem 24, 445–454 (2013). https://doi.org/10.1007/s11224-012-0097-9

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  • DOI: https://doi.org/10.1007/s11224-012-0097-9

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