Crystal Structures of β-Cyclodextrin Complexes with Formic Acid and Acetic Acid View Full Text


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Article Info

DATE

2003-10

AUTHORS

Thammarat Aree, Burkhard Schulz, Günter Reck

ABSTRACT

β-Cyclodextrin (β–CD)-formic acid (1) andβ-CD–acetic acid (2) inclusion complexes crystallizeas β-CD...0.3HCOOH...7.7H2O andβ-CD...0.4CH3COOH...7.7H2O in themonoclinic space group P21 with comparable unit cell constants.Anisotropic refinement of atomic parameters against X-ray diffractiondata with Fo2 > 2σ (Fo2) (986/8563 and 991/8358)converged at R-factors of 0.051 and 0.054 for 1 and 2,respectively. In both complexes, the β-CD molecularconformation, hydration pattern and crystal packing are similar,but the inclusion geometries of the guest molecules are different.The β-CD macrocycles adopt a ``round'' conformationstabilized by intramolecular, interglucose O3(n)...O2(n + 1)hydrogen bonds and their O6–H groups are systematically hydratedby water molecules. In the asymmetric unit, each complex contains oneβ-CD, 0.3 formic acid (or 0.4 acetic acid), and 7.7 water moleculesthat are distributed over 9 positions. Water sites located in theβ-CD cavity hydrogen bond to the guest molecule. In thecrystal lattice, β-CD molecules are packed in a typical ``herringbone'' fashion. In 1, the formic acid (occupancy 0.3) is entirely included in the β-CD cavity such that its C atom is shifted from the O4-plane center to the β-CD O6-side by 2.90 Å and C=O, C–-O bonds point to this side. In 2, the acetic acid (occupancy 0.4) is completely embedded in the β-CD cavity, in which the carboxylic C atom is displaced from the O4-plane centerto the β-CD O6-side by 0.87 Å; the C=O bond directsto the β-CD O6-side and makes an angle of 15°to the β-CD molecular axis. Furthermore, bothdimethyl-β-CD-acetic acid and β-CD-acetic acidcomplexes form a cage structure, showing that the small guestsenclosed entirely in the cavity either in β-CD or indimethyl-β-CD do not affect the packing of the host macrocycles. More... »

PAGES

39-45

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/b:jiph.0000003923.92981.0f

DOI

http://dx.doi.org/10.1023/b:jiph.0000003923.92981.0f

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1012436145


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