Conformationally mobile wide rim carbamoylmethylphosphine oxide (CMPO)-calixarenes

Matthews, Susan E. ORCID:, Saadioui, Mohamed, Böhmer, Volker, Barboso, Silvia, Arnaud-Neu, Françoise, Schwing-Weill, Marie-José, Garcia Carrera, Alejandro and Dozol, Jean-François (1999) Conformationally mobile wide rim carbamoylmethylphosphine oxide (CMPO)-calixarenes. Journal für praktische Chemie, 341 (3). pp. 264-273.

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Six new calix[4]arene derivatives 2a–f have been synthesised, bearing CMPO-like functions (-NH–C(O)–CH2–P(O)Ph2) at their wide rim. They differ by their alkoxy groups at the narrow rim, comprising all possible combinations of methoxy and syn-propoxy groups including the conformationally mobile tetramethyl ether 2e and the tetrapropyl ether 2f fixed in the cone conformation. Their extraction behaviour for thorium(IV) and several lanthanides(III) from 1M HNO3 to dichloromethane has been studied and compared also to non cyclic calixarene analogues 6a–e. Surprisingly the best extraction results were found for the 1,2-dimethoxy-3,4-dipropoxy derivative 2c among the calixarenes and for the tetramer 6d among the linear compounds. Extraction of americium(III) in comparison to curium(III) and various lanthanides(LaIII), Ce(III), Nd(III), Sm(III), Eu(III)) from 0.1– 3M HNO3 to NPHE (o-nitrophenyl hexyl ether) was most effective again for 2c. Among these cations, the highest distribution coefficients were found for Am(III) and the lowest for Ce(III) with a maximum generally in the range of 1–2M HNO3.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
UEA Research Groups: Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017)
Depositing User: Sophie Buckingham
Date Deposited: 03 Mar 2013 22:13
Last Modified: 15 Dec 2022 01:58
DOI: 10.1002/(SICI)1521-3897(199904)341:3<264::AID-PRAC264>3.3.CO;2-6

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