An insight into intramolecular blue-shifting CH⋯π hydrogen bonds in 1,3-Hexadien-5-yne. (cas 10420-90-3)and its halogen-substituted derivatives

Add time:07/31/2019    Source:sciencedirect.com

The blue-shifting intramolecular CH⋯π hydrogen bonds (H-bonds) in conformer I of 1,3-hexadien-5-yne (13HD5Y) and its halogen-substituted derivatives are explored by theoretical calculations. The geometric analysis indicates that the CH bond in conformer I is shortened in comparison with the non-interacting CH bond, accompanied by the blue-shifts of the CH stretching frequency. The formation of H-bonds is verified by the atoms-in-molecules and noncovalent interaction analysis. The H-bond energies are estimated to be −0.5∼−2.2 kcal·mol−1 by isodesmic reaction method at MP2/aug-cc-pVTZ level, which agree with the trends predicted by the geometrical and topological parameters. The results of the natural bond orbital analysis indicate that the origin of the blue-shifting H-bond may be due to the weak π(CC) → σ*(CH) hyperconjugation interaction and the concomitant increasing in the s-character and polarization of CH bond. This research provides a rare theoretical evidence to identify an intramolecular blue-shifting CH⋯π H-bond system.

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