The effect of number and position of P=O/P=S bridging units on cavitand selectivity toward methyl ammonium salts

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Daniela MenozziEnrico Dalcanale

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.

References

Jan 26, 2008·Chemical Communications : Chem Comm·Elina KaleniusPirjo Vainiotalo
Mar 28, 2008·Chemical Communications : Chem Comm·Elisa BiavardiEnrico Dalcanale
May 21, 2008·Chemistry : a European Journal·Monica MelegariEnrico Dalcanale
May 13, 2009·Journal of the American Chemical Society·Elisa BiavardiEnrico Dalcanale
Jan 14, 2012·Journal of the American Chemical Society·Marco DionisioPaolo Bergese
Feb 7, 2012·Proceedings of the National Academy of Sciences of the United States of America·Elisa BiavardiEnrico Dalcanale

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Citations

Dec 19, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Roberta Pinalli, Chiara Massera

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Methods Mentioned

BETA
Quartz Crystal Microbalance
column chromatography
X-ray
NMR

Software Mentioned

97
SHELXL
SIR97
WinGX
TWINABS
SAINT
SQUEEZE

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