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Two dibenzodiazepinone molecules with dissimilar dimeric associations and apparent different tautomeric forms
Max Keller1, Mohan M Bhadbhade, Roger W Read
1School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia.
Summary
Dibenzodiazepinones exhibit dimeric association through hydrogen bonds. The parent compound exists in the lactam form, while its derivative shows potential for lactim tautomerism, influencing their structures.
Area of Science:
- Crystallography
- Organic Chemistry
- Medicinal Chemistry
Background:
- Dibenzodiazepinones are tricyclic compounds with potential pharmaceutical applications.
- Understanding their structural and tautomeric properties is crucial for drug design.
Purpose of the Study:
- To investigate the dimeric association and tautomeric forms of a parent dibenzodiazepinone and its acylated derivative.
- To elucidate the structural differences and driving forces behind their configurations.
Main Methods:
- X-ray crystallography was used to determine the solid-state structures.
- Analysis of hydrogen bonding patterns and bond lengths to identify tautomeric forms.
Main Results:
- The parent compound, 5H-dibenzo[b,e]diazepin-11(10H)-one, forms dimers via N-H...O hydrogen bonds in the lactam tautomeric form.
- The acylated derivative forms dimers with unique crystallographic molecules, suggesting potential lactim tautomerism.
- Structural differences were observed in the cyclic amide entities and their hydrogen bonding.
Conclusions:
- Dibenzodiazepinone derivatives exhibit distinct dimeric associations and tautomeric preferences.
- Hydrogen bonding and molecular structure significantly influence the configurations of these compounds.
- The findings provide insights into the structure-activity relationships of dibenzodiazepinones.
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