ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Evaluating role of the x–π (x = π and/or CH) stacking interactions in adsorption of the (4E,4E)-4-(4-hydroxyphenyldiazenyl)-N-((furan-2-Yl)methylene)benzenamine antibacterial in armchair boron nitride nanotube

Samireh Esmaeili, Marjaneh Samadizadeh, and Mehrnoosh Khaleghian

Department of Chemistry, Islamic Azad University, Tehran, Iran

E-mail: samira200016@yahoo.com

Received: 25 August 2019  Accepted: 16 March 2020

Abstract:

Non-covalent interactions have been investigated in several orientations of (4E,4E)-4-(4-hydroxyphenyldiazenyl)-N-((furan-2-yl)methylene)benzenamine/armchair single-wall boron nitride nanotube [EE-HPDFMB/SWBNNT] complexes at ωB97X-D/6-31G(d) level of theory. Global reactivity indexes show electrophile and nucleophile roles of EE-HPDFMB and SWBNNT, respectively. This result confirms molecular electrostatic potential maps and low HOMO_SWBNNT–LUMO_EE-HPDFMB gap. These interactions as weak forces can cause a physical adsorption and encapsulation of EE-HPDFMB with medicinal properties in the SWBNNT. More negative values (− 25.7 and − 47.2 kJ mol⁻¹) of adsorption energy including zero point energy and basis set superposition error corrections ((D_{ ext{e}}^{0})) in the inside complexes show better adsorption strength, stable configuration and small red shift than outside. This issue mainly results from existence of the several π–π and CH–π stacking interactions in the inside complexes. More importantly, obtained electron density ρ(r) and Laplacian ∇²ρ(r) from QTAIM analysis reveal that the π–π stacking in the inside is stronger than outside complex. Low second-order stabilization energies in the in/outside complexes are confirmation for these non-covalent interactions in electron view point.

Keywords: π–π and CH–π stacking; Boron nitride nanotube; QTAIM analysis; NBO analysis; Molecular electrostatic potential (MEP)

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01137-x

Chemical Papers 74 (9) 2991–3000 (2020)