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Impacts of medium, substituents, and specific interactions with water on hydration of carbonyl compounds

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Abstract

Theoretical study on hydration of carbonyl compounds has been done at B3LYP/6-31++G** and MP2/6-31++G** levels. The variations in ΔG hyd and hydration constants are explored in terms of medium effect, substituent effect, and hydrogen bonding abilities of carbonyl compounds and their hydrated products. The dielectric of medium decreases the ΔG hyd values thereby favoring the process. The presence of electron-releasing substituents at the carbonyl carbon disfavors the hydration process, while that of electron-withdrawing substituents favor the process. Hydrogen bonding interactions stabilize the product to a larger extent than the carbonyl molecules, thereby favoring the hydration process. Linear correlation between the calculated log K hyd values and the experimental values is seen in case of specific interactions with water (R = 0.976) than in the case without those interactions (R = 0.955).

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Acknowledgments

The authors are highly thankful to DST (INSPIRE Fellowship Programme) for the financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, Guru Nanak Dev University, Amritsar, 143005, India

    Damanjit Kaur, Rajinder Kaur & Shweta Khanna

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  1. Damanjit Kaur
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  2. Rajinder Kaur
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  3. Shweta Khanna
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Correspondence to Damanjit Kaur.

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Kaur, D., Kaur, R. & Khanna, S. Impacts of medium, substituents, and specific interactions with water on hydration of carbonyl compounds. Struct Chem 25, 437–450 (2014). https://doi.org/10.1007/s11224-013-0308-z

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  • DOI: https://doi.org/10.1007/s11224-013-0308-z

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