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Stability and molecular properties of the boron-nitrogen alternating analogs of azulene and naphthalene: a computational study

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Abstract

In this work, the spectroscopic information, stability and aromaticity of the boron-nitrogen azulene and naphthalene molecules are provided by the use of CC2 (geometry optimization, dipole moment, UV–vis spectrum calculations) and DFT (vibrational spectrum and NMR calculations) methodologies. One isomer of the investigated boron-nitrogen naphthalene (boroazanaphthalene) and two isomers of boron-nitrogen azulene, 1,3,4,6,8-pentaaza-2,3a,5,7,8a-pentaboraazulene (BN-azulene) and 2,3a,5,7,8a-pentaaza-1,3,4,6,8- pentaboraazulene (NB-azulene), are stable systems. However, these molecules have different properties, i.e., different stability, dipole moment, and aromaticity based on the NICS approach. BN-naphthalene has a high dipole moment magnitude showing high polar character, while naphthalene is apolar. BN- and NB-azulene are weakly polar, while ordinary azulene is highly polar in character. Also, substitution of C atoms by B and N atoms decreases the aromaticity. In the case of NB-azulene, the seven-membered ring has anti-aromaticity behavior while both rings of BN-azulene exhibit aromaticity. We expect that the new theoretical data provided in this work will be useful in identifying and characterizing experimentally the compounds investigated, and in helping our understanding of the chemistry of boron-nitrogen molecules.

Boron-nitrogen alternating analogs of azulene. Spectral distinction between isomers

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Acknowledgments

The authors are grateful for the financial support given by CAPES Foundation (Coordenação de Aperfeiçoamento de Pessoal de Nível superior), the São Paulo Research Foundation (FAPESP, Fundação de Amparo a Pesquisa do Estado de São Paulo) Grant 2010/11385-2 and by the CNPq (Brazilian Science Funding Agencies).

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  1. Departamento de Química, Universidade Federal de São Carlos (UFSCar), São Carlos, SP, 13560-970, Brazil

    Anderson José Lopes Catão & Alejandro López-Castillo

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  1. Anderson José Lopes Catão
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Correspondence to Anderson José Lopes Catão.

Electronic supplementary material

The ESM contains all geometric parameters as well as dipole moment orientation and vertical transition of BN-azulene, NB-azulene and BN-naphthalene molecules. A population analysis of the azulene molecule is also presented for comparison purposes.

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Catão, A.J.L., López-Castillo, A. Stability and molecular properties of the boron-nitrogen alternating analogs of azulene and naphthalene: a computational study. J Mol Model 23, 119 (2017). https://doi.org/10.1007/s00894-017-3279-y

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