An Exceptionally Close, Non-Bonded Hydrogen-Hydrogen Contact with Strong Through-Space Spin-Spin Coupling

Yonglong Xiao; Joel T Mague; Robert A Pascal Jr

doi:10.1002/anie.201712304

An Exceptionally Close, Non-Bonded Hydrogen-Hydrogen Contact with Strong Through-Space Spin-Spin Coupling

Angew Chem Int Ed Engl. 2018 Feb 19;57(8):2244-2247. doi: 10.1002/anie.201712304. Epub 2018 Jan 26.

Authors

Yonglong Xiao¹, Joel T Mague¹, Robert A Pascal Jr¹

Affiliation

¹ Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.

PMID: 29328535
DOI: 10.1002/anie.201712304

Abstract

Condensation of 1,8,13-tris(mercaptomethyl)triptycene and tris(bromomethyl)methane yields an in,in-cyclophane with two inwardly directed methine groups. Based on X-ray analysis and DFT and MP2 calculations, the hydrogen-hydrogen non-bonded contact distance is estimated to be 1.50-1.53 Å. Furthermore, the two in-hydrogen atoms show obvious spin-spin coupling with J=2.0 Hz.

Keywords: cyclophanes; in/out stereoisomerism; non-bonded contacts; through-space spin-spin coupling.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.