2,4,6,8-Tetraazabicyclo[3.3.1]nonane-3,7-dione and 2,4,6,8-Tetraacetyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione

Piacenza, Guy; Beguet, C.; Wimmer, E.; Gallo, R.; Giorgi, Michel

doi:10.1107/s0108270197006495

Cited by 6 publications

(5 citation statements)

References 1 publication

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“…We sought a more appropriate complement to the right angles of the cavitand and arrived at propanediurea 4 . The corresponding angle of 4 (Figure c) is ∼99°, and we expected its smooth integration into 1.1 . Typical self-assembly processes that incorporate multiple subunits create cavity shapes of high symmetry such as spheres, polyhedra, and cylinders.…”

Section: Slightly Different Spacersmentioning

confidence: 81%

More Chemistry in Small Spaces

2012

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This Account is about coaxing molecules into spaces barely big enough to contain them: encapsulation complexes. In capsules, synthetic modules assemble to fold around their molecular targets, isolate them from the medium for relatively long times, place them in a hydrophobic environment, and present them with functional groups. These arrangements also exist in the interior spaces of biology, and the consequences include the familiar features of enzymes: rapid reactions, stabilization of reactive intermediates, and catalysis. But inside capsules there are phenomena unknown to biology or historical chemistry, including new structures, new stereochemical relationships, and new reaction pathways. In encapsulation complexes, as in architecture, the space that is created by a structure determines what goes on inside. There are constant interactions between the container and contained molecules: encounters are not left to chance; they are prearranged, prolonged, and intense. Unlike architecture, these reversibly formed containers emerge only when a suitable guest is present. The components exist, but they cannot assemble without anything inside. Modifications of the capsule components give rise to the results of the present Account. The focus will be on how seemingly small changes in the encapsulation complexes, exchanging a C═S for a C═O, reducing an angle here and there, or replacing a hydrogen with a methyl, can lead to unexpectedly large differences in behavior.

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Section: Slightly Different Spacersmentioning

confidence: 81%

More Chemistry in Small Spaces

2012

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“…The corresponding angle of the propanediurea 3 (Figure 1 c) is smaller (ca. 99°)14 and more appropriate as a complement to the right angles of the cavitand. Accordingly, we expected the interaction of 1.1 and 3 but were nonetheless surprised by the results.…”

Section: Packing Coefficients (Pc) For Encapsulated Alkane Guests Thmentioning

confidence: 99%

Self‐Assembled Capsules of Unprecedented Shapes

2011

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“…The salt was removed by passing the solution through ion-exchange resin (Amberlyst A-26 OH) to obtain Me 10 prCB [5] in a yield of 1%. The resulting macrocycle was unequivocally analyzed by 1 H and 13 C NMR spectrometry and MS spectrometry. Absence of the salt in the macrocycle was checked using 1 H NMR in DMSO-d 6 solution (for details, see Figure S8, Supporting Information).…”

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confidence: 99%

“…As a result, prCB[5] differs from CB[5] not only in diameter but also in depth. We were inspired by the work of Nolte et al, who used propanediurea in the construction of molecular clips. , The distance between two oxygen atoms in the propanediurea is about 0.57 Å smaller compared to glycoluril. − It was reported that this rather small difference in the geometry has a pronounced effect on the affinity of molecular clips toward dihydroxybenzenes . Propanediureas resemble the structural features of glycolurils, except for the additional methylene bridge between the two methine carbons.…”

mentioning

confidence: 99%