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Theoretical studies of inclusion complexes of α‐ and β‐cyclodextrin with benzoic acid and phenol
Author(s) -
Huang MingJu,
Watts John D.,
Bodor Nicholas
Publication year - 1997
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/(sici)1097-461x(1997)65:6<1135::aid-qua12>3.0.co;2-4
Subject(s) - benzoic acid , chemistry , cyclodextrin , phenol , intramolecular force , intermolecular force , computational chemistry , stereochemistry , crystallography , organic chemistry , molecule
A series of semiempirical molecular orbital calculations using the AM1 method were performed on the inclusion complexes of α‐ and β‐cyclodextrin with benzoic acid and phenol in the “head‐first” and “tail‐first” positions. The AM1 results show that α‐cyclodextrin complexes with both guest compounds in the “head first” position are more stable than in the “tail‐first” position, while the β‐cyclodextrin complex with phenol in the “tail‐first” position is more stable, but with benzoic acid, the “head‐first” position is more stable. The driving forces for complex formation were investigated based on different intramolecular and intermolecular interactions. In addition, 1SCF AM1 calculations were performed on the β‐cyclodextrin complexes with benzoic acid in the “tail‐first” and “head‐first” positions with the benzoic acid moved stepwise along the Z ‐axis of the β‐cyclodextrin principal axis coordinate system. © 1997 John Wiley & Sons, Inc. Int J Quant Chem 65 : 1135–1152, 1997