Stability and electronic properties of binary systems involving hydrogen and halogen bonded [12]cyclacenes: a DFT study
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ORIGINAL RESEARCH
Stability and electronic properties of binary systems involving hydrogen and halogen bonded [12]cyclacenes: a DFT study Hamid Reza Masoodi 1 & Sotoodeh Bagheri 1 Received: 15 May 2020 / Accepted: 9 June 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract The [n]cyclacene as a class of aromatic nanobelts can be considered for synthesizing new compounds. Here, the binary systems involving hydrogen and halogen bonded [12]cyclacenes are investigated at M06-2X/6-311++G(d,p) level of theory. The calculations are performed in gas phase and in water and acetone solvents. Because of their opportunities for the various applications in materials science, some electronic properties such as HOMO–LUMO gap, electronic chemical potential, first ionization energy, electron affinity, electrophilicity index, chemical hardness, and softness are examined. The role of hydrogen and halogen bonds on stability of dyads is also studied by atoms in molecules (AIM) theory. Keywords Aromatic nanobelts . [n]cyclacene . Belt[n]arenes . Hydrogen bond . Halogen bond
Introduction Hydrogen bond is one of the most common intermolecular interactions and plays a crucial role in biology, physics, and chemistry [1, 2]. Although the hydrogen bond is often considered as an electrostatic dipole-dipole interaction, it has some properties, similar to covalent bonding, such as it is directional and strong, and interatomic distances in products are shorter than the sum of the van der Waals radii. The covalent features are amplified when the electronegativity of hydrogen donor increases [1]. The halogen bond is a kind of non-covalent interaction and plays a distinctive role in molecular recognition, crystal engineering, and biomolecular systems [3, 4]. A halogen bond occurs between the positive potential of halogen atom and the negative Lewis base center. Hydrogen and halogen bonds can respectively be described in general as A···H −D and A···X−D. In both cases, A is the atom, group, or molecule that donates electrons to the electron poor species H−D or X−D. H and X are the electrophilic hydrogen and halogen atoms involved in hydrogen and halogen bonding, respectively. D is a carbon, nitrogen, oxygen, or halogen atom [2, 5]. Halogen bonding is classified as a subset of σ-hole * Hamid Reza Masoodi [email protected]; [email protected] 1
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, P.O. Box 77176, Rafsanjan, Iran
interactions. The formation of non-covalent interactions can be described using the σ-hole concept [6]. The size of the σhole on the halogen, σ-hole interaction angle, donor atom properties, and internuclear distance between halogen and halogen bond acceptor can affect the strength of halogen bond [7, 8]. Although electrostatic term has a key role to determine features and properties of halogen bond, polarization, charge transfer, and dispersion terms also play an important role [9]. Hydrogen and halogen bonds were extensively examined to design new materials [
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