Organic Letters

, volume 22 , issue 1 , pages 204-208

Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

Pravat Mondal ^{1, 2}

Ephrath Solel ²

Shubhanjan Mitra ^{1, 2}

Ehud Keinan ²

O. Reany ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Department of Natural Sciences, The Open University of Israel, Ra’anana 4353701, Israel |

The Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 3200003, Israel |

Publication type: Journal Article

Publication date: 2019-12-17

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.9b04166

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PubMed ID: 31846336

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

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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DSc in Chemistry

506 publications, 7 606 citations, 1 review

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A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

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GOST |

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GOST Copy

Mondal P. et al. Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse // Organic Letters. 2019. Vol. 22. No. 1. pp. 204-208.

GOST all authors (up to 50) Copy

Mondal P., Solel E., Mitra S., Keinan E., Reany O. Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse // Organic Letters. 2019. Vol. 22. No. 1. pp. 204-208.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.9b04166

UR - https://doi.org/10.1021/acs.orglett.9b04166

TI - Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

T2 - Organic Letters

AU - Mondal, Pravat

AU - Solel, Ephrath

AU - Mitra, Shubhanjan

AU - Keinan, Ehud

AU - Reany, O.

PY - 2019

DA - 2019/12/17

PB - American Chemical Society (ACS)

SP - 204-208

IS - 1

VL - 22

PMID - 31846336

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Mondal,

author = {Pravat Mondal and Ephrath Solel and Shubhanjan Mitra and Ehud Keinan and O. Reany},

title = {Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse},

journal = {Organic Letters},

year = {2019},

volume = {22},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/acs.orglett.9b04166},

number = {1},

pages = {204--208},

doi = {10.1021/acs.orglett.9b04166}

}

MLA

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MLA Copy

Mondal, Pravat, et al. “Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse.” Organic Letters, vol. 22, no. 1, Dec. 2019, pp. 204-208. https://doi.org/10.1021/acs.orglett.9b04166.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)

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