Halogen bonds on substituted dibromonitrobenzene derivatives
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ORIGINAL PAPER
Halogen bonds on substituted dibromonitrobenzene derivatives Ricardo R. Ternavisk 1 & Vitor S. Duarte 1,2 & Jean M. F. Custódio 1,3 & Gerardo A. Hernández 4 & José A. Romero 4 & Ademir J. Camargo 1 & Hamilton B. Napolitano 1,5 Received: 21 May 2020 / Accepted: 8 October 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Halogen bonding is a noncovalent interaction that has attracted great attention because of its importance in several areas, such as photonics, nonlinear optics, pharmaceutical products, supramolecular engineering, biochemistry, protein–ligand complexes, and polymer interactions. In this context, we describe the synthesis, molecular structure, supramolecular arrangement, and theoretical calculations of five dibromonitrobenzene derivatives, which present different halogen atoms substituted. The solid-state characterization was carried out by X-ray diffraction with the contribution of Hirshfeld surfaces for analysis of molecular interactions. The frontier molecular orbital, molecular electrostatic potential, and quantum theory of atoms in molecules were carried out at the M06-2X/6-311+G(d,p) level of theory. Those observed halogen interactions indicate the crystalline solid-state stabilization for the dibromonitrobenzene derivatives. Keywords Dibromonitrobenzene derivatives . X-ray diffraction . Halogen bonding . DFT
Introduction Halogen bonding could be considered as a noncovalent interaction between an electrophilic region from a halogen atom This paper belongs to Topical Collection XX - Brazilian Symposium of Theoretical Chemistry (SBQT2019) Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00894-020-04566-3) contains supplementary material, which is available to authorized users. * Ricardo R. Ternavisk [email protected] * Gerardo A. Hernández [email protected] * Hamilton B. Napolitano [email protected] 1
Grupo de Química Teórica e Estrutural de Anápolis, Universidade Estadual de Goiás, Anapolis, GO, Brazil
2
Centro de Pesquisa e Eficiência Energética, CAOA Montadora de Veículos LTDA, Anapolis, GO, Brazil
3
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN, USA
4
Instituto Tecnológico de Tijuana, Centro de Graduados e Investigación en Química, Tijuana, BC, Mexico
5
Laboratório de Novos Materiais, Centro Universitário de Anápolis, Anapolis, GO, Brazil
and a nucleophilic region from a neighboring molecule [1–3]. The halogen atom acts as an electrophile, despite its high electronegativity [1], attracting considerable attention in supramolecular engineering [2, 3]. This class of interactions plays an essential role in biochemistry [4], such as protein– ligand complexes [5], enzyme-substrate interactions, polymer interactions [6], and the design of new materials (in photonics, nonlinear optics, and pharmaceutics) [6–9]. The anisotropic distribution of electron density on the atom concentrated along the covalent bond induces an electron deficiency on the opposite
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