Head to Tail Distortion Wave Characterizes the Enantiomerization of Helicenes

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 compu...

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Published in:Journal of organic chemistry 2020-12, Vol.85 (23), p.15415-15421
Main Authors: Kaspi-Kaneti, Ariela W, Barroso, Jorge, Merino, Gabriel, Avnir, David, Garzón, Ignacio L, Tuvi-Arad, Inbal
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cited_by cdi_FETCH-LOGICAL-a333t-1e4acb8d9cb3d2e80c9b07ddbf1594a8d623574f306a12b394b681708248e5983
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container_end_page 15421
container_issue 23
container_start_page 15415
container_title Journal of organic chemistry
container_volume 85
creator Kaspi-Kaneti, Ariela W
Barroso, Jorge
Merino, Gabriel
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Garzón, Ignacio L
Tuvi-Arad, Inbal
description 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.
doi_str_mv 10.1021/acs.joc.0c02196
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title Head to Tail Distortion Wave Characterizes the Enantiomerization of Helicenes
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