Weak hydrogen bonding. Part 5. Experimental evidence for the long-range nature of CC–H ⋯π interactions: crystallographic and spectroscopic studies of three terminal alkynes

Thomas Steiner; Matthias Tamm; Alexander Grzegorzewski; Niels Schulte; Nora Veldman; Antoine M. M. Schreurs; Jan A. Kanters; Jan Kroon; John van der Maas; Bert Lutz

doi:10.1039/P29960002441

Weak hydrogen bonding. Part 5. Experimental evidence for the long-range nature of CC–H ⋯π interactions: crystallographic and spectroscopic studies of three terminal alkynes

Thomas Steiner, Matthias Tamm, Alexander Grzegorzewski, Niels Schulte, Nora Veldman, Antoine M. M. Schreurs, Jan A. Kanters, Jan Kroon, John van der Maas and Bert Lutz

Abstract

In the crystal structures of three terminal alkynes, long C [triple bond, length half m-dash] C–H ⋯ CC contacts with H ⋯ C separations in the range 2.7–3.1 Å are observed. Despite the long distances, these contacts possess the characteristic infrared spectroscopic features of weak hydrogen bonds. This provides direct evidence that the range of C–H ⋯π interactions donated by sufficiently acidic C–H groups extends beyond van der Waals separation. In two of the crystal structures, the C–H ⋯π interactions form interconnected systems C [triple bond, length half m-dash] C–H ⋯ CC–H ⋯ CC–H.

Journal of the Chemical Society, Perkin Transactions 2

Weak hydrogen bonding. Part 5. Experimental evidence for the long-range nature of CC–H ⋯π interactions: crystallographic and spectroscopic studies of three terminal alkynes

Abstract

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Weak hydrogen bonding. Part 5. Experimental evidence for the long-range nature of CC–H ⋯π interactions: crystallographic and spectroscopic studies of three terminal alkynes

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