Molecular recognition and effects of steric and geometric isomerism. Thermodynamic study of non-bonding interactions in aqueous solutions of cycloalkanols

1996 ◽  
Vol 92 (7) ◽  
pp. 1149 ◽  
Author(s):  
Giuseppina Castronuovo ◽  
Vittorio Elia ◽  
Filomena Velleca
Keyword(s):  
Molecular Recognition ◽  
Aqueous Solutions ◽  
Thermodynamic Study ◽  
Geometric Isomerism

scholarly journals Molecular recognition of N-acetyltryptophan enantiomers by β-cyclodextrin

2017 ◽  
Vol 13 ◽  
pp. 1572-1582 ◽  
Author(s):  
Spyros D Chatziefthimiou ◽  
Mario Inclán ◽  
Petros Giastas ◽  
Athanasios Papakyriakou ◽  
Konstantina Yannakopoulou ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Molecular Recognition ◽  
Aqueous Solutions ◽  
Crystalline State ◽  
Dimeric Complex ◽  
Nmr Studies ◽  
Guest Molecules ◽  
Crystallographic Order

The enantioselectivity of β-cyclodextrin (β-CD) towards L- and D-N-acetyltryptophan (NAcTrp) has been studied in aqueous solution and the crystalline state. NMR studies in solution show that β-CD forms complexes of very similar but not identical geometry with both L- and D-NAcTrp and exhibits stronger binding with L-NAcTrp. In the crystalline state, only β-CD–L-NAcTrp crystallizes readily from aqueous solutions as a dimeric complex (two hosts enclosing two guest molecules). In contrast, crystals of the complex β-CD–D-NAcTrp were never obtained, although numerous conditions were tried. In aqueous solution, the orientation of the guest in both complexes is different than in the β-CD–L-NAcTrp complex in the crystal. Overall, the study shows that subtle differences observed between the β-CD–L,D-NAcTrp complexes in aqueous solution are magnified at the onset of crystallization, as a consequence of accumulation of many soft host–guest interactions and of the imposed crystallographic order, thus resulting in very dissimilar propensity of each enantiomer to produce crystals with β-CD.

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