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


Celik Bayar C., Turker L.

POLYCYCLIC AROMATIC COMPOUNDS, vol.40, no.4, pp.1266-1279, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 40 Issue: 4
  • Publication Date: 2020
  • Doi Number: 10.1080/10406638.2020.1749088
  • Journal Name: POLYCYCLIC AROMATIC COMPOUNDS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Agricultural & Environmental Science Database, Applied Science & Technology Source, CAB Abstracts, Communication Abstracts, Food Science & Technology Abstracts, Metadex, Pollution Abstracts, Veterinary Science Database, Civil Engineering Abstracts
  • Page Numbers: pp.1266-1279
  • Keywords: (R)-Hexahelicene, M06-2X, NICS(1), trinitrotoluene (TNT), pi-pi interaction, THEORETICAL INSIGHTS, DFT, THERMOCHEMISTRY, TESTOSTERONE, CHEMOSENSOR, HELICENES, STACKING, GRAPHENE, SENSOR, QSAR
  • Middle East Technical University Affiliated: Yes

Abstract

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 pi-pi 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 pi-pi interactions with TNT.