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Synthesis, spectral and RAHB studies on some arylhydrazones of β-diketones: crystal and molecular structures of 2-(2-(3-pyridyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione and 2-(2-(2-methoxyphenyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione

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Abstract

The present study describes the synthesis and spectral analysis of a series of arylhydrazones of β-diketones (1–6) along with the single crystal X-ray structural studies of 2-(2-(3-pyridyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione (3) and 2-(2-(2-methoxyphenyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione (6). Spectral and structural studies clearly exemplify the effective intramolecular hydrogen bonding and as a result the NH proton signals and carbonyl carbon signals are shifted to higher frequency region in NMR spectra. Structural implications imposed by the formation of pseudo six-membered ring after hydrogen bonding is well observed in XRD analysis. XRD analysis also evidences the envelop conformation of the dimedone ring in both the cases and resonance assisted hydrogen bonding (RAHB) studies were also performed.

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Acknowledgments

The authors are extremely thankful to Prof. Dr. K. Ramalingam of Annamalai University for his valuable suggestions regarding the X-ray structural analysis.

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Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalainagar, 608002, Tamil Nadu, India

    Annamalai Sethukumar & Balasubramaniyam Arul Prakasam

  2. Chemical Crystallography Laboratory, P.G. Department of Physics, University of Jammu, Jammu Tawi, 180006, India

    Sabeta Kohli & Rajnikant Verma

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  1. Annamalai Sethukumar
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  2. Balasubramaniyam Arul Prakasam
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  3. Sabeta Kohli
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  4. Rajnikant Verma
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Correspondence to Balasubramaniyam Arul Prakasam.

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Sethukumar, A., Arul Prakasam, B., Kohli, S. et al. Synthesis, spectral and RAHB studies on some arylhydrazones of β-diketones: crystal and molecular structures of 2-(2-(3-pyridyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione and 2-(2-(2-methoxyphenyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione. Struct Chem 22, 23–33 (2011). https://doi.org/10.1007/s11224-010-9677-8

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  • DOI: https://doi.org/10.1007/s11224-010-9677-8

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