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Molecules 2015, 20(3), 4460-4472; doi:10.3390/molecules20034460

The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts

Dipartimento di Chimica, Università di Parma and INSTM UdR Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy
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Academic Editor: David B. Smithrud
Received: 12 February 2015 / Revised: 2 March 2015 / Accepted: 5 March 2015 / Published: 10 March 2015
(This article belongs to the Special Issue Host-Guest Chemistry)
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Abstract

The present work reports the synthesis and complexation properties of five mixed bridge P=O/P=S cavitands toward N,N-methyl butyl ammonium chloride (1) as prototype guest. The influence of number and position of P=O and P=S groups on the affinity of phosphonate cavitands toward 1 is assessed via ITC titrations in DCE as solvent. Comparison of the resulting Kass values, the enthalpic and entropic contributions to the overall binding with those of the parent tetraphosphonate Tiiii and tetrathiophosphonate TSiiii cavitands allows one to single out the simultaneous dual H-bond between the cavitand and the salt as the major player in complexation. View Full-Text
Keywords: phosphonate cavitands; thiophosphonate cavitands; mixed-bridged cavitands; molecular recognition; N,N-methyl alkyl ammonium salts; ITC phosphonate cavitands; thiophosphonate cavitands; mixed-bridged cavitands; molecular recognition; N,N-methyl alkyl ammonium salts; ITC
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Menozzi, D.; Pinalli, R.; Massera, C.; Maffei, F.; Dalcanale, E. The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts. Molecules 2015, 20, 4460-4472.

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