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Substitution effects in phenyl and N-pyrrole derivatives along the periodic table

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Abstract

A theoretical study of the monosubstitution effects of all the atoms of the second and third row of the periodic table on the phenyl and pyrrole rings has been carried out by means of B3LYP/6-31 + G(d,p) DFT calculations. The geometric and electronic properties, calculated using the Atoms In Molecules methodology, have been analyzed. Some of the results have been rationalized based on the electronegativity of the substituents. In addition, the different parameters obtained have been compared with different aromaticity indexes (HOMA, NICS, and ASE), as well as with Taft’s σ0 R parameter.

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Acknowledgments

This work was carried out with financial support from the Ministerio de Ciencia y Tecnología (Project No. CTQ2006-14487-C02-01/BQU) and Comunidad Autónoma de Madrid (Project MADRISOLAR, ref. S-0505/PPQ/0225). Thanks are given to the CTI (CSIC) for allocation of computer time.

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Authors and Affiliations

  1. Faculty of Chemistry, Jagiellonian University, 3 Ingardena Street, Krakow, 30-060, Poland

    Krzysztof Zborowski

  2. Instituto de Química Médica (C.S.I.C.), Juan de la Cierva, 3, Madrid, 28006, Spain

    Ibon Alkorta & José Elguero

Authors
  1. Krzysztof Zborowski
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  2. Ibon Alkorta
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  3. José Elguero
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Correspondence to Ibon Alkorta.

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Dedicated to Professor Tadeusz Marek Krygowski on his 70th birthday.

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Zborowski, K., Alkorta, I. & Elguero, J. Substitution effects in phenyl and N-pyrrole derivatives along the periodic table. Struct Chem 18, 797–805 (2007). https://doi.org/10.1007/s11224-007-9245-z

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  • DOI: https://doi.org/10.1007/s11224-007-9245-z

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