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Theoretical and Experimental Studies of the Inclusion Phenomena of β ‐Cyclodextrin with Organic Amines
Author(s) -
SONG LeXin,
WANG HaiMing,
TENG ChuanFeng,
BAI Lei,
XU Peng,
GUO XueQing
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890308
Subject(s) - chemistry , ethylenediamine , aqueous solution , cyclodextrin , intermolecular force , diethylenetriamine , binding energy , triethylamine , inclusion compound , amine gas treating , interaction energy , inclusion (mineral) , computational chemistry , organic chemistry , molecule , physics , mineralogy , nuclear physics
The inclusion complexations of β ‐cyclodextrin ( β ‐CD) with ethylenediamine 1 and its three analogs, diethylenetriamine 2 , triethylamine 3 and ethylene diaminetetraacetic acid 4 were examined by means of both experimental measurements and theoretical calculations. From the polarimetric method, it was found that β ‐CD could form 1/1 host‐guest inclusion complexes with these guests, and the formation constants ( K ) of the inclusion complexes have also been determined in aqueous solution at 298.2 K. Semiempirical PM3 calculations were carried out to assess the intermolecular binding ability of β ‐CD to a series of short chain aliphatic amines such as guests 1 – 7 , cyclic aliphatic amines 8 – 11 , and aromatic amines 12 – 13 . The interaction processes between β ‐CD and the guests were reported, and the complexation differences of β ‐CD with these guests also discussed. The energy contribution from deformation energy or hydrate energy to interaction energy in the inclusion systems was found to be quite small. The stability of β ‐CD inclusion complexes depended on the size fit between the host and guest. For β ‐CD complexes of guests 1 – 4, the order of the K values from the polarimetric measurements is in good accordance with that of the absolute values of the complexation energies from PM3 calculations.