Mixed chiral and achiral character in substituted ethane: A next generation QTAIM perspective

• Published in: Chemical physics letters 2022-09, Vol.803, p.139762, Article 139762
• Main Authors: Li, Zi, Xu, Tianlv, Früchtl, Herbert, van Mourik, Tanja, Kirk, Steven R., Jenkins, Samantha
• Format: Article
• Language: English
• Subjects: Achiral; Chiral; Ethane; Halogen; Next Generation QTAIM
• ISSN: 0009-2614
• DOI: 10.1016/j.cplett.2022.139762

The singly F-substituted ethane C1-C2 bond critical point (BCP) stress tensor trajectories Tσ(s) for the Cartesian CW and CCW torsions for the Sσ and Rσ (left-panel) Uσ-space stereoisomers. The corresponding Tσ(s) for the doubly F-Cl substituted ethane C1-C2 BCP stereoisomers that possesses a high degree of achiral character in Uσ-space. [Display omitted] •NG-QTAIM used to investigate the chirality of singly and doubly substituted ethane.•The singly and doubly substituted ethane comprised the halogen atoms F, Cl, Br.•BCP sliding of singly substituted ethane highly dependent on halogen atomic number.•Doubly substituted Sa and Ra stereoisomers comprised mixed Uσ-space chirality.•Highest achirality in Uσ-space of doubly substituted ethane caused by F substituent. We use the newly introduced spanning stress tensor trajectory Uσ-space construction within next generation quantum theory of atoms in molecules (NG-QTAIM) for a chirality investigation of singly and doubly substituted ethane with halogen substituents: F, Cl, Br. Singly substituted ethane was overall achiral comprising cancelling chiral components in Uσ-space. The resultant axial bond critical point (BCP) sliding responded more strongly to the increase in atomic number of the substituted halogen than the chirality. The presence of the very light F atom was found responsible for a very high degree of achiral character of the doubly substituted ethane.