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Mixed Solvent Chemistry through Synergistic Solvation: Structure, Property and Function of t-Butanol—Dichloromethane Binary Solvent Mixtures

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Abstract

The present study elucidates the synergetic solvation behavior of t-butanol–dichloromethane (t-BuOH–DCM) binary solvent mixtures. UV–visible absorption, emission and 1H-NMR spectroscopy along with analytical modelling were used to ascertain the nature of interactions present, which are found to be maximum at X t-BuOH = 0.40, leading to a super solvation environment. The increased polarity of the t-BuOH–DCM binary solvent mixtures through interactive solvent association is believed provide a unique reaction medium that can alter the fate of chemical processes involving a polar species. This idea has been demonstrated by the transformation of merocyanine to 1′,3′-dihydro-,1′,3′,3′-trimethyl-6-nitropiro[2H-1-benzopyran-2,2′-(2H)-indole] and the oxidation of cholestanol to cholestanone.

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Acknowledgements

SG and KNP thank CSIR (Council of Scientific and Industrial Research, India) and PM thanks UGC (University Grants Commission, India) for awarding a fellowship. We thank Professor J. N. Moorthy for his help to conduct the cholestanol oxidation study in his laboratory and for providing cholestanol and TetMe-IBX. This work is financially supported by the Science and Engineering Research Board, Department of Science and Technology, Government of India (Project No. SR/S1/PC-08/2011) and IIT Kanpur.

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  1. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP, 208 016, India

    Shradhey Gupta, Keshaba Nanda Parida, Puspal Mukherjee & Pratik Sen

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  1. Shradhey Gupta
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  2. Keshaba Nanda Parida
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Correspondence to Pratik Sen.

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10953_2017_586_MOESM1_ESM.docx

Description of flash photolysis setup, plots of absorption and emission spectra of coumarin 480 in different compositions of t-BuOH–DCM binary solvent mixture, 1H-NMR of DCM proton and –OH proton of t-BuOH with varying mole fraction of t-BuOH in t-BuOH–DCM binary solvent mixture, procedure for oxidation of cholestanol to cholestanone by tetramethyl-IBX. (DOCX 585 kb)

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Gupta, S., Parida, K.N., Mukherjee, P. et al. Mixed Solvent Chemistry through Synergistic Solvation: Structure, Property and Function of t-Butanol—Dichloromethane Binary Solvent Mixtures. J Solution Chem 46, 461–475 (2017). https://doi.org/10.1007/s10953-017-0586-y

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