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

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...

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Autores principales: Menozzi, Daniela, Pinalli, Roberta, Massera, Chiara, Maffei, Francesca, Dalcanale, Enrico
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272763/
https://www.ncbi.nlm.nih.gov/pubmed/25764488
http://dx.doi.org/10.3390/molecules20034460
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author Menozzi, Daniela
Pinalli, Roberta
Massera, Chiara
Maffei, Francesca
Dalcanale, Enrico
author_facet Menozzi, Daniela
Pinalli, Roberta
Massera, Chiara
Maffei, Francesca
Dalcanale, Enrico
author_sort Menozzi, Daniela
collection PubMed
description 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.
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spelling pubmed-62727632018-12-31 The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts Menozzi, Daniela Pinalli, Roberta Massera, Chiara Maffei, Francesca Dalcanale, Enrico Molecules Article 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. MDPI 2015-03-10 /pmc/articles/PMC6272763/ /pubmed/25764488 http://dx.doi.org/10.3390/molecules20034460 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Menozzi, Daniela
Pinalli, Roberta
Massera, Chiara
Maffei, Francesca
Dalcanale, Enrico
The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts
title The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts
title_full The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts
title_fullStr The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts
title_full_unstemmed The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts
title_short The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts
title_sort effect of number and position of p=o/p=s bridging units on cavitand selectivity toward methyl ammonium salts
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272763/
https://www.ncbi.nlm.nih.gov/pubmed/25764488
http://dx.doi.org/10.3390/molecules20034460
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