NDLI: The role of hydrogen bonding in pseudo-macrocyclic ring formation in 2,6-dimethyl-1,3,5,7-cyclooctatetraene 1,3,5,7-tetracarboxylic acid monohydrate

Content Provider	Springer Nature Link
Author	Vij, Ashwani Palmer, Jennifer L. Chauhan, Kamlesh Williams, Richard Vaughan
Copyright Year	2000
Abstract	2,6-Dimethyl-1,3,5,7-cyclooctatetraene-1,3,5,7-tetracarboxylic acid 3, C$_{14}$H$_{14}$O$_{9}$, was prepared by thermolysis of the corresponding semibullvalene and characterized by spectroscopic and single-crystal X-ray diffraction studies. The monohydrate of 3 crystallizes in the tetrahedral space group P-4n2, a = 11.0924(3) Å, c = 12.6799(5) Å, V = 1560.15(9) Å$^{3}$, Z = 4. The cyclooctatetraene ring adopts a tub-shaped conformation with a crystallograpically imposed twofold rotational symmetry, and is composed of localized C=C double bonds in the 1,3,5, and 7 positions with an average interatomic distance of 1.327 (5) Å and C–C single bonds with an average interatomic distance of 1.489(5) Å. The average C=C–C angle in the ring is 122.6(3)°. Each symmetry generated eight-membered ring contains four carboxyl groups, two of which are coplanar with the methyl groups across the C=C ring atoms. However, across the C–C bonds the carboxyl groups and the methyl groups show a torsion angle of 64.3(4)°. The presence of a water molecule in the crystal lattice generates a three-dimensional network of close hydrogen bondings between water and the carboxyl groups of multiple rings. This creates a network of orthogonal 10-membered rings between the 8-membered rings. Two given cyclooctatetraene rings are intermolecularly hydrogen bonded not only directly through their carboxyl groups but also via a bridging water molecule. This effect is rare in polycarboxylic acids and their monohydrates which bond only with water or among themselves.
Starting Page	621
Ending Page	626
Page Count	6
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	30
Issue Number	10
e-ISSN	15728854
Language	English
Publisher	Kluwer Academic Publishers-Plenum Publishers
Publisher Date	2000-01-01
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Inorganic Chemistry Physical Chemistry Crystallography
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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