Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Theoretically Predicted and Experimentally Detected Chirality of Dibenzocycloctynes and of their Triazole Adducts with Azides.

Version 1 : Received: 18 January 2023 / Approved: 19 January 2023 / Online: 19 January 2023 (09:13:54 CET)

How to cite: Mazzoccanti, G.; Franzini, R.; Ciogli, A.; Pierini, M.; Faggi, C.; Francioso, A.; Villani, C. Theoretically Predicted and Experimentally Detected Chirality of Dibenzocycloctynes and of their Triazole Adducts with Azides.. Preprints 2023, 2023010352. https://doi.org/10.20944/preprints202301.0352.v1 Mazzoccanti, G.; Franzini, R.; Ciogli, A.; Pierini, M.; Faggi, C.; Francioso, A.; Villani, C. Theoretically Predicted and Experimentally Detected Chirality of Dibenzocycloctynes and of their Triazole Adducts with Azides.. Preprints 2023, 2023010352. https://doi.org/10.20944/preprints202301.0352.v1

Abstract

Dibenzocycloctynes have emerged as a promising scaffold for bioorthogonal ligation. An important structural aspect that has not been addressed so far is connected with their chirality. Herein, we explore by theoretical and experimental methods this structural aspect that has been so far neglected. First, a computational analysis is conducted and results are used as a guideline for experimental investigation. Next, an array of different experiments (HPLC on chiral columns, chiroptical spectroscopy, X-ray diffraction) for structure elucidation are scrutinized in concert. Finally, this work demonstrates the chirality and the stereodynamic behavior of dibenzocycloctynes and of their triazole adducts with simple azides and uncover their conformational behavior.

Keywords

conformational chiralty; atropisomers; racemization; xray structure; circular dichroism; computa-tional

Subject

Chemistry and Materials Science, Organic Chemistry

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