On the Nature of CH⋅⋅⋅FC Interactions in Hindered CF₃C(sp³) Bond Rotations

Abstract

In Chinaalkaloidgerüsten wurden gehinderte CF3‐Rotationen beobachtet. Die Variation der CF3‐Rotationsbarrierehöhen wird durch die jeweiligen Entropieänderungen gesteuert, wenn ein Allylsubstituent durch eine sperrige 9‐Methylanthracenylgruppe ersetzt wird. Quantenchemische und experimentelle Studien ergaben, dass die nichtkovalenten C3′‐H1⋅⋅⋅F‐C‐Wechselwirkungen in den untersuchten Fällen einen schwachen H‐Brückencharakter haben.

Crystal structure of 2-[(dichloromethane)sulfonyl]pyridine

“…For the biological activity of sulfone derivatives, see: Chen et al (2012); Drews (2000); Raja et al (2009). For the uses of halomethyl sulfone derivatives in organic synthesis, see: Li & Hu (2005); Prakash et al (2013); Zhao et al (2010). For the synthesis of the starting material, see: Kamiyama et al (1988 Table 1 Hydrogen-bond geometry (Å , ).…”

“…Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008) Sulfonyl groups are well-known for imparting biological activities to a lot of natural and unnatural molecules (Chen, et al, 2012;Drews, 2000;Raja, et al, 2009). Besides, halomethyl sulfones have been widely used in the preparation of a wide variety of halogenated compounds (Li & Hu, 2005;Prakash, et al, 2013;Zhao, et al, 2010). Here, we report the crystal structure of 2-(dichloromethylsulfonyl)pyridine, the title compound, which may find potential use in the synthesis of interesting chlorinated compounds.…”