Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril

Elena Prigorchenko; Sandra Kaabel; Triin Narva; Anastassia Baškir; Maria Fomitšenko; Jasper Adamson; Ivar Järving; Kari Rissanen; Toomas Tamm; Riina Aav

doi:10.1039/c9cc04990h

Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril

Elena Prigorchenko, Sandra Kaabel, Triin Narva, Anastassia Baškir, Maria Fomitšenko, Jasper Adamson, Ivar Järving, Kari Rissanen, Toomas Tamm, Riina Aav^*

^*Corresponding author for this work

Not published at Aalto University

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

6 Citations (Scopus)

Abstract

Formation of inverted-cis-cyclohexanohemicucurbit[6]uril (i-cis-cycHC[6]), with up to 33% isolated yield, can be induced at the expense of thermodynamically favoured cis-cycHC[6]. Reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous precipitation of the formed macrocycles. Different binding affinities of three diastereomeric cycHC[6]s with trifluoroacetic acid is demonstrated.

Original language	English
Pages (from-to)	9307-9310
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	63
DOIs	https://doi.org/10.1039/c9cc04990h
Publication status	Published - 2019
MoE publication type	A1 Journal article-refereed

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title = "Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril",

abstract = "Formation of inverted-cis-cyclohexanohemicucurbit[6]uril (i-cis-cycHC[6]), with up to 33% isolated yield, can be induced at the expense of thermodynamically favoured cis-cycHC[6]. Reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous precipitation of the formed macrocycles. Different binding affinities of three diastereomeric cycHC[6]s with trifluoroacetic acid is demonstrated.",

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year = "2019",

doi = "10.1039/c9cc04990h",

language = "English",

volume = "55",

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journal = "Chemical Communications",

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T1 - Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril

AU - Prigorchenko, Elena

AU - Kaabel, Sandra

AU - Narva, Triin

AU - Baškir, Anastassia

AU - Fomitšenko, Maria

AU - Adamson, Jasper

AU - Järving, Ivar

AU - Rissanen, Kari

AU - Tamm, Toomas

AU - Aav, Riina

PY - 2019

Y1 - 2019

N2 - Formation of inverted-cis-cyclohexanohemicucurbit[6]uril (i-cis-cycHC[6]), with up to 33% isolated yield, can be induced at the expense of thermodynamically favoured cis-cycHC[6]. Reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous precipitation of the formed macrocycles. Different binding affinities of three diastereomeric cycHC[6]s with trifluoroacetic acid is demonstrated.

AB - Formation of inverted-cis-cyclohexanohemicucurbit[6]uril (i-cis-cycHC[6]), with up to 33% isolated yield, can be induced at the expense of thermodynamically favoured cis-cycHC[6]. Reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous precipitation of the formed macrocycles. Different binding affinities of three diastereomeric cycHC[6]s with trifluoroacetic acid is demonstrated.

UR - http://www.scopus.com/inward/record.url?scp=85070849641&partnerID=8YFLogxK

U2 - 10.1039/c9cc04990h

DO - 10.1039/c9cc04990h

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AN - SCOPUS:85070849641

VL - 55

SP - 9307

EP - 9310

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 63

ER -

Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril

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