Investigation of π-π Interactions between TNT and (R)-Hexahelicene

• Published in: Polycyclic aromatic compounds Vol. 40; no. 4; pp. 1266 - 1279
• Main Authors: Celik Bayar, Caglar, Turker, Lemi
• Format: Journal Article
• Language: English
• Published: Philadelphia Taylor & Francis 07.08.2020; Taylor & Francis Ltd
• Subjects: (R)-Hexahelicene; 2,4,6-Trinitrotoluene; Aromatic compounds; Aromaticity; Circular dichroism; Dichroism; M06-2X; Military applications; Molecular orbitals; NICS; Orbital stability; Stability analysis; trinitrotoluene (TNT); π-π interaction
• ISSN: 1040-6638; 1563-5333
• DOI: 10.1080/10406638.2020.1749088

The detection of an energetic molecule TNT is an important issue especially in military applications and as a result many of the studies focused on this subject in the literature. In this study, except from the literature, the possible interactions between TNT and polycyclic aromatic chiral compound (R)-Hexahelicene were examined theoretically in terms of non-covalent π-π interactions, theoretically. It was observed that (R)-Hexahelicene had such interactions with TNT via the 2nd and 3rd six-membered rings of its exterior surface. NICS(1) aromaticity analyses, interaction energy calculations, interaction energy-NICS(1) relationships, UV-visible and electronic circular dichroism analyses and frontier molecular orbital analyses with reactivity and stability predictions were all performed to make sure that such interactions may occur between the suggested couples. A hybrid DFT functional of M06-2X was used with 6-31 + G(d,p) basis set throughout the study. It was concluded that (R)-Hexahelicene may serve as a good surface to make π-π interactions with TNT.