Head to Tail Distortion Wave Characterizes the Enantiomerization of Helicenes

The Journal of Organic Chemistry
Ariela W Kaspi-KanetiInbal Tuvi-Arad

Abstract

A fresh look on helicenes' enantiomerization process with a focus on ring conformation reveals that it can be described as a step-by-step mechanism in which maximal distortion is consecutively transferred along the helicene skeleton, head to tail. Density functional theory methods were used to compute the enantiomerization pathway, and continuous symmetry measures were applied to quantify the distortion of even-number helicenes with 8-14 rings. Our findings show that the distortion wave is additive-the process always starts from one edge of the helicene and progresses along the rings until the other edge is reached. As more rings are added to the helicene, extra steps are appended to the distortion wave. Implications of this fundamental process are discussed in light of similar natural phenomena from polymer dynamics to snake locomotion.

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Citations

Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Carlos Emiliano Buelna-GarcíaJose Luis Cabellos

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