Weak noncovalent interactions in 1,2,4-triazole-3-thione-linked adamantyl derivatives: experimental and computational insights into their potential as antiproliferative agents.

ABSTRACT: The synthesis, single-crystal X-ray structures, and antiproliferative activity of five adamantyl-linked 1,2,4-triazole-3-thione derivatives are presented. The crystal structures of the mono- and di-substituted chloro derivatives were analyzed in detail, revealing a variety of weak noncovalent interactions, including C-H···N, C-H···O, C-H···Cl, C-H···S, and π···π stacking, which contribute to the stability of their supramolecular assemblies. Notably, the crystal packing is also stabilized by σ-hole interactions, such as S···S and S···N chalcogen bonds, and by short, attractive Csp³-H···H-Csp³ contacts involving the adamantyl moieties. The nature and energetics of these interactions were investigated through a combination of Hirshfeld surface analysis, generalized Kohn-

SUBMITTER: Al-Wahaibi LH 

PROVIDER: S-EPMC12703193 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature