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The diketo form of (+)-(1R,4R)-3-benzoylcamphor

✍ Scribed by Seo, Jang Woo ;Niemeyer, Mark

Book ID: 104488154
Publisher: International Union of Crystallography
Year: 2006
Tongue: English
Weight: 204 KB
Volume: 62
Category: Article
ISSN: 1600-5368
DOI: 10.1107/s1600536806039808

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✦ Synopsis

Molecules of the title compound, (+)-(1R,4R)-3-benzoyl-1,7,7trimethylbicyclo[2.2.1]heptan-2-one, C 17 H 20 O 2 , crystallize in the diketo form. One of the carbonyl groups is involved in a weak intramolecular C-HÁ Á ÁO interaction [CÁ Á ÁO = 2.778 (3) A ˚]. 3-Benzoylcamphor is a rare example of a structurally characterized -diketone that crystallizes both in the diketo and the enol forms. According to density functional theory (DFT) calculations, the diketo tautomer is destabilized by 17.4 kJ mol À1 over the previously reported [Niemeyer & Gan (2005). Acta Cryst. E61, o2363-o2365] enol form.

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The diketo form of (+)-(1R,4R)-3-benzoyl­camphor

✦ Synopsis

The diketo form of (+)-(1R,4R)-3-benzoylcamphor