Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

Pravat Mondal; Ephrath Solel; Shubhanjan Mitra; Ehud Keinan; Ofer Reany

doi:10.1021/acs.orglett.9b04166

Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

Pravat Mondal, Ephrath Solel, Shubhanjan Mitra, Ehud Keinan, Ofer Reany

Chemistry discipline

Research output: Contribution to journal › Article › peer-review

Abstract

This study confirms the hypothesis that bambusurils (BUs) with equatorial sulfur atoms cannot assume an anion-binding jigger conformation due to strong intramolecular van der Waals attractive interactions. NMR, X-ray crystallography, and computation with newly synthesized eq-semithio-BU[4] and ax-semiaza-eq-semithio-BU[4]s indicate that they all assume compact conformations. Intramolecular distances and a torsional angle serve as reliable indicators of the conformation of any BU. Chemoselective alkylation at the peripheral (equatorial) thiourea functions provides a convenient entry to novel hetero-BUs.

Original language	English
Pages (from-to)	204-208
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.9b04166
State	Published - 3 Jan 2020

Bibliographical note

Funding Information:
The authors are grateful for financial support from Israel Ministry of Science Technology and Space (MOST) Grant 3-10855 and the Open University of Israel (OUI). The authors thank Dr. Natalia Fridman from the crystallographic lab at the Schulich Faculty of Chemistry, Technion, for her valuable contribution to the X-ray crystallographic efforts.

Publisher Copyright:
© 2019 American Chemical Society.

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abstract = "This study confirms the hypothesis that bambusurils (BUs) with equatorial sulfur atoms cannot assume an anion-binding jigger conformation due to strong intramolecular van der Waals attractive interactions. NMR, X-ray crystallography, and computation with newly synthesized eq-semithio-BU[4] and ax-semiaza-eq-semithio-BU[4]s indicate that they all assume compact conformations. Intramolecular distances and a torsional angle serve as reliable indicators of the conformation of any BU. Chemoselective alkylation at the peripheral (equatorial) thiourea functions provides a convenient entry to novel hetero-BUs.",

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Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

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