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

Molecules

Daniela Menozzi²  Roberta Pinalli²  Chiara Massera²  Francesca Maffei²  Enrico Dalcanale¹ 

[1] Dipartimento di Chimica, Università di Parma and INSTM UdR Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy;

关键词: phosphonate cavitands;    thiophosphonate cavitands;    mixed-bridged cavitands;    molecular recognition;    N;    N-methyl alkyl ammonium salts;    ITC;   

DOI  :  10.3390/molecules20034460

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.