Insights into Thiol-Aromatic Interactions: A Stereoelectronic Basis for S-H/π Interactions.

ABSTRACT: Thiols can engage favorably with aromatic rings in S-H/π interactions, within abiological systems and within proteins. However, the underlying bases for S-H/π interactions are not well understood. The crystal structure of Boc-l-4-thiolphenylalanine tert-butyl ester revealed crystal organization centered on the interaction of the thiol S-H with the aromatic ring of an adjacent molecule, with a through-space H_thiol···C_aromatic distance of 2.71 Å, below the 2.90 Å sum of the van der Waals radii of H and C. The nature of this interaction was further examined by DFT calculations, IR spectroscopy, solid-state NMR spectroscopy, and analysis of the Cambridge Structural Database. The S-H/π interaction was found to be driven significantly by favorable molecular orbital interact

SUBMITTER: Forbes CR 

PROVIDER: S-EPMC5890429 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature