Contact Ion Pairs on a Protonated Azamacrocycle: the Role of the Anion Basicity

Fraschetti, Caterina; Filippi, Antonello; Crestoni, Maria Elisa; Marcantoni, Enrico; Glucini, Marco; Guarcini, Laura; Montagna, Maria; Guidoni, Leonardo; Speranza, Maurizio

doi:10.1007/s13361-015-1327-3

Cited by 3 publications

(2 citation statements)

References 45 publications

(49 reference statements)

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“…The determination of the enantiomeric excess of different carboxylic acids has been achieved on the basis of good splitting of the NMR signals for the enantiomers of the bound guest molecules [50][51][52][53]. Interestingly, in the gas phase, amine 15 is able to bind potassium cations, anions, such as carboxylates, but also to function as an acceptor of contact K + /anion pairs [54,55]. Lead(II) complexes of macrocycles 9, 10, 12, and 13 can be reduced and demetallated to give the corresponding free macrocyclic amines 15-18 (Figure 8).…”

Section: [2 + 2] Macrocyclesmentioning

confidence: 99%

“…The determination of the enantiomeric excess of different carboxylic acids has been achieved on the basis of good splitting of the NMR signals for the enantiomers of the bound guest molecules [50][51][52][53]. Interestingly, in the gas phase, amine 15 is able to bind potassium cations, anions, such as carboxylates, but also to function as an acceptor of contact K + /anion pairs [54,55]. The formation of [2 + 2] imines is preferred when enantiopure DACH is condensed with dialdehydes based on two benzaldehyde fragments that are connected by a link X (Figure 9) which enforces the bent conformation of the dialdehyde.…”

Section: [2 + 2] Macrocyclesmentioning

confidence: 99%

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Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

Lisowski

2022

Molecules

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The condensation of aromatic dialdehydes with chiral diamines, such as 1,2-trans-diaminocyclohexane, leads to various enantiopure or meso-type macrocyclic Schiff bases, including [2 + 2], [3 + 3], [4 + 4], [6 + 6] and [8 + 8] condensation products. Unlike most cases of macrocycle synthesis, the [3 + 3] macrocycles of this type are sometimes obtained in high yields by direct condensation without a metal template. Macrocycles of other sizes from this family can often be selectively obtained in high yields by a suitable choice of metal template, solvent, or chirality of the building blocks. In particular, the application of a cadmium(II) template results in the expansion of the [2 + 2] macrocycles into giant [6 + 6] and [8 + 8] macrocycles. These imine macrocycles can be reduced to the corresponding macrocyclic amines which can act as hosts for the binding of multiple cations or multiple anions.

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Section: [2 + 2] Macrocyclesmentioning

confidence: 99%

“…The determination of the enantiomeric excess of different carboxylic acids has been achieved on the basis of good splitting of the NMR signals for the enantiomers of the bound guest molecules [50][51][52][53]. Interestingly, in the gas phase, amine 15 is able to bind potassium cations, anions, such as carboxylates, but also to function as an acceptor of contact K + /anion pairs [54,55]. The formation of [2 + 2] imines is preferred when enantiopure DACH is condensed with dialdehydes based on two benzaldehyde fragments that are connected by a link X (Figure 9) which enforces the bent conformation of the dialdehyde.…”

Section: [2 + 2] Macrocyclesmentioning

confidence: 99%

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

Lisowski

2022

Molecules

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Synthesis of [2+2] Schiff base macrocycles by a solvent templating strategy and halogen bonding directed assembly

Taylor

Kilah

2022

J Incl Phenom Macrocycl Chem

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Schiff base imine condensations are a useful tool for macrocycle synthesis and applications within supramolecular chemistry. Here we address the mixtures of products that can arise from template free synthesis using dicarbonylheterocycles and diamines, and look to develop metal-free template methods for selective macrocycle formation. A range of alkyl α,ω-diamines were combined with phenanthroline and pyridine heterocyclic dicarbaldehydes under standard literature conditions. The reaction conditions were modified to demonstrate a relationship between choice of solvent and product equilibria. It was observed that benzene and toluene could shift a mixture of products and unreacted starting materials to form predominantly one imine product for a number of systems. Once the macrocyclic products had been characterized in selected solvents, iodinated halogen bonding guest molecules were added to direct macrocycle assemblies using non-covalent interactions. Studies to investigate host – guest suitability and halogen bond interactions were conducted, and it was found that tetraiodoethylene had an influence on the formation of a phenanthroline based macrocycle. Proof of concept experiments were performed to show the influence of the guest molecule, tetraiodoethylene, on the macrocyclic products formed under competitive dynamic combinatorial chemistry conditions.

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Reactivity of contact ion pairs in a charged monotopic receptor

Filippi

Crestoni

Fraschetti

et al. 2017

International Journal of Mass Spectrometry

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Contact Ion Pairs on a Protonated Azamacrocycle: the Role of the Anion Basicity

Abstract: , is able to add in the gas phase mono-and dicarboxylate anions as well as inorganic anions by forming the corresponding monocharged adducts, the structure of which markedly depends on the basicity of the anion.

Cited by 3 publications

References 45 publications

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

Synthesis of [2+2] Schiff base macrocycles by a solvent templating strategy and halogen bonding directed assembly

Reactivity of contact ion pairs in a charged monotopic receptor

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