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2,6-Dimethyl-4-m-tolyl-cyclo-hex-3-enecarboxylic acid.

ABSTRACT: The title compound, C(16)H(20)O(2), was synthesized to study the hydrogen-bonding inter-action of the two enanti-omers in the solid state. The racemate is made up of carboxylic acid RS dimers. Inter-molecular O-H?O hydrogen bonds produce centrosymmetric R(2) (2)(8) rings which dimerize the two chiral enanti-omers through their carboxyl groups. The chirality of this compound is generated by the presence of the double bond in the cyclo-hexene ring and a chiral axis due to the meta-methyl substituent on the aromatic ring.

SUBMITTER: Xie S 

PROVIDER: S-EPMC2959375 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

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2,6-Dimethyl-4-m-tolyl-cyclo-hex-3-enecarboxylic acid.

Xie Songwen S   Stein Holly J HJ   Pink Maren M  

Acta crystallographica. Section E, Structure reports online 20080906 Pt 10

The title compound, C(16)H(20)O(2), was synthesized to study the hydrogen-bonding inter-action of the two enanti-omers in the solid state. The racemate is made up of carboxylic acid RS dimers. Inter-molecular O-H⋯O hydrogen bonds produce centrosymmetric R(2) (2)(8) rings which dimerize the two chiral enanti-omers through their carboxyl groups. The chirality of this compound is generated by the presence of the double bond in the cyclo-hexene ring and a chiral axis due to the meta-methyl substitue  ...[more]

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