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EnglishA combined XRD and 1H NMR study revealed that two molecules of tetrakis-(tert-butyloxycarbonylmethoxy)-calixij5]arene carboxylic acid are able to efficiently encapsulate α,ω-diaminoalkanes of suitable length as a result of proton-transfer-mediated recognition. In the case of 1,10-diaminodecane and 1,11-diaminoundecane, rim-to-rim attractive van der Waals interactions drive the formation of capsular complexes with a packing coefficient close to 70%. The two calixarene bowls in these capsules are seen in an eclipsed conformation. On the other hand, when the longer 1,12-diaminododecane guest is used, a quasi-capsular complex is formed in which the capsule seal is lost and the two calixarenes are arranged in a staggered conformation as a result of a reciprocal rotation of the two facing macrocyclic cavities. A comparison with similar capsular complexes confirms that a hydrophobic ‘bayonet-mount’ fastening is mandatory for the encapsulation of suitably sized guests.
| Titolo: | α,ω-Alkanediyldiammonium dications sealed within calix[5]arene capsules with a hydrophobic bayonet-mount fastening |
| Autori: | PISAGATTI, Ilenia (Ultimo) |
| Data di pubblicazione: | 2015 |
| Rivista: | |
| Abstract: | A combined XRD and 1H NMR study revealed that two molecules of tetrakis-(tert-butyloxycarbonylmethoxy)-calixij5]arene carboxylic acid are able to efficiently encapsulate α,ω-diaminoalkanes of suitable length as a result of proton-transfer-mediated recognition. In the case of 1,10-diaminodecane and 1,11-diaminoundecane, rim-to-rim attractive van der Waals interactions drive the formation of capsular complexes with a packing coefficient close to 70%. The two calixarene bowls in these capsules are seen in an eclipsed conformation. On the other hand, when the longer 1,12-diaminododecane guest is used, a quasi-capsular complex is formed in which the capsule seal is lost and the two calixarenes are arranged in a staggered conformation as a result of a reciprocal rotation of the two facing macrocyclic cavities. A comparison with similar capsular complexes confirms that a hydrophobic ‘bayonet-mount’ fastening is mandatory for the encapsulation of suitably sized guests. |
| Handle: | http://hdl.handle.net/11570/3063549 |
| Appare nelle tipologie: | 14.a.1 Articolo su rivista |
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| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| CEC_2015,17,7915-7921.pdf | cec2015 | Versione Editoriale (PDF) | Tutti i diritti riservati (All rights reserved) | Utenti riconosciuti Richiedi una copia |
http://hdl.handle.net/11570/3063549
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