Croconamides: A new dual hydrogen bond donating motif for anion recognition and organocatalysis

Anne Jeppesen; Bjarne Enrico Nielsen; Dennis Larsen; Olivia M. Akselsen; Theis Ivan Sølling; Theis Brock-Nannestad; Michael Pittelkow

doi:10.1039/c7ob00441a

Croconamides: A new dual hydrogen bond donating motif for anion recognition and organocatalysis

Anne Jeppesen, Bjarne Enrico Nielsen, Dennis Larsen, Olivia M. Akselsen, Theis Ivan Sølling, Theis Brock-Nannestad, Michael Pittelkow^*

^*Corresponding author for this work

Department of Chemistry

13 Citations (Scopus)

Abstract

We introduce bis-aryl croconamides as a new member in the family of dual hydrogen bonding anion receptors. In this study a series of croconamides are synthesised, and the selectivity for anion binding is investigated (Cl^- > Br^- > I^- in CH₂Cl₂). The croconamides exhibit different structures in the crystal phase depending on the substituents on the aromatic rings, and furthermore, the crystal structure revealed the presence of tautomers. DFT calculations elucidated the complex structures formed upon addition of anion to the croconamides, confirming the order of association constants towards the halogen anions. The use of croconamides as organocatalysts in a proof-of-concept study is demonstrated in the formation of THP ethers. In addition to this, construction of a Hammet plot further elucidates the mechanism in action on formation of THP ethers.

Original language	English
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	13
Pages (from-to)	2784-2790
Number of pages	7
ISSN	1477-0520
DOIs	https://doi.org/10.1039/c7ob00441a
Publication status	Published - 2017

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title = "Croconamides: A new dual hydrogen bond donating motif for anion recognition and organocatalysis",

abstract = "We introduce bis-aryl croconamides as a new member in the family of dual hydrogen bonding anion receptors. In this study a series of croconamides are synthesised, and the selectivity for anion binding is investigated (Cl- > Br- > I- in CH2Cl2). The croconamides exhibit different structures in the crystal phase depending on the substituents on the aromatic rings, and furthermore, the crystal structure revealed the presence of tautomers. DFT calculations elucidated the complex structures formed upon addition of anion to the croconamides, confirming the order of association constants towards the halogen anions. The use of croconamides as organocatalysts in a proof-of-concept study is demonstrated in the formation of THP ethers. In addition to this, construction of a Hammet plot further elucidates the mechanism in action on formation of THP ethers.",

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year = "2017",

doi = "10.1039/c7ob00441a",

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T1 - Croconamides

T2 - A new dual hydrogen bond donating motif for anion recognition and organocatalysis

AU - Jeppesen, Anne

AU - Nielsen, Bjarne Enrico

AU - Larsen, Dennis

AU - M. Akselsen, Olivia

AU - Sølling, Theis Ivan

AU - Brock-Nannestad, Theis

AU - Pittelkow, Michael

PY - 2017

Y1 - 2017

N2 - We introduce bis-aryl croconamides as a new member in the family of dual hydrogen bonding anion receptors. In this study a series of croconamides are synthesised, and the selectivity for anion binding is investigated (Cl- > Br- > I- in CH2Cl2). The croconamides exhibit different structures in the crystal phase depending on the substituents on the aromatic rings, and furthermore, the crystal structure revealed the presence of tautomers. DFT calculations elucidated the complex structures formed upon addition of anion to the croconamides, confirming the order of association constants towards the halogen anions. The use of croconamides as organocatalysts in a proof-of-concept study is demonstrated in the formation of THP ethers. In addition to this, construction of a Hammet plot further elucidates the mechanism in action on formation of THP ethers.

AB - We introduce bis-aryl croconamides as a new member in the family of dual hydrogen bonding anion receptors. In this study a series of croconamides are synthesised, and the selectivity for anion binding is investigated (Cl- > Br- > I- in CH2Cl2). The croconamides exhibit different structures in the crystal phase depending on the substituents on the aromatic rings, and furthermore, the crystal structure revealed the presence of tautomers. DFT calculations elucidated the complex structures formed upon addition of anion to the croconamides, confirming the order of association constants towards the halogen anions. The use of croconamides as organocatalysts in a proof-of-concept study is demonstrated in the formation of THP ethers. In addition to this, construction of a Hammet plot further elucidates the mechanism in action on formation of THP ethers.

U2 - 10.1039/c7ob00441a

DO - 10.1039/c7ob00441a

M3 - Journal article

C2 - 28272644

AN - SCOPUS:85016291802

SN - 1470-4358

VL - 15

SP - 2784

EP - 2790

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 13

ER -

Croconamides: A new dual hydrogen bond donating motif for anion recognition and organocatalysis

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