Inclusion Compounds of Dehydrocholic Acid with Solvents

Marco Fogagnolo,Olga Bortolini,Giancarlo Fantin

doi:10.3390/i8070662

Marco Fogagnolo, Olga Bortolini + Show 1 more

Open Access

https://doi.org/10.3390/i8070662

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Abstract

The host-guest inclusion of various organic solvents within dehydrocholic acid has been studied and the selectivity of enclathration determined by competition experiments.

Highlights

The process of selective enclathration has been studied in a variety of host-guest systems and bile acids have shown a particular ability in the inclusion of organic guest molecules as aliphatic and aromatic hydrocarbons, alcohols, ketones, esters, nitriles, epoxides, amides etc [1]
In recent years we have studied the inclusion ability of dehydrocholic acid 1 for the resolution of organic racemates [2] of aryl methyl sulfoxides [3] and cyclic amides [4], including the precise definition of the different structures involving the sole host or the host-guest assemblies [5]
The α-form crystallizes in such a way that two independent molecules are linked in dimers by two hydrogen bonds between the carboxylic acid groups at C-24, whereas in the β form two hydrogen bonds are formed between the carboxylic acid functionality and the carbonyl group at C-3

Summary

Introduction

The process of selective enclathration has been studied in a variety of host-guest systems and bile acids have shown a particular ability in the inclusion of organic guest molecules as aliphatic and aromatic hydrocarbons, alcohols, ketones, esters, nitriles, epoxides, amides etc [1]. In recent years we have studied the inclusion ability of dehydrocholic acid 1 for the resolution of organic racemates [2] of aryl methyl sulfoxides [3] and cyclic amides [4], including the precise definition of the different structures involving the sole host or the host-guest assemblies [5]. In this frame, it was found that dehydrocholic acid may be obtained in two polymorphic forms, α and β, the latter being thermodynamically more stable [6]. Competition between couples of these guests with 1 and the related selectivities have been determined [7]

Inclusion compounds

IR analysis

Thermal analysis

Competition experiments

Experimental Section