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C–H···Y (Y=N, O, π) Hydrogen Bond: A Unique Unconventional Hydrogen Bond

  • Review Article
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Journal of the Indian Institute of Science Aims and scope

Abstract

We present a spectroscopic overview of the C–H···Y (Y = hydrogen bond acceptors) hydrogen bonded (HB or H-bond) complexes in this article. Although C–H···Y interactions have been recognized as H-bonding interactions for quite some time, they have not been investigated spectroscopically until recently. Recent results indicated that unlike the conventional hydrogen bond, C–H···Y H-bond has interesting spectroscopic characteristics, i.e. it shows both red as well as blue shift in C–H stretching frequency upon H-bond formation. This review presents examples of red, blue, and zero shifted C–H···Y H-bonds investigated in our laboratory that were characterized using laser-based IR and UV spectroscopic techniques applied to the cold isolated molecular complexes formed under supersonic expansion conditions. Along with spectroscopic information, ab initio/DFT-predicted geometry optimized structures of various conformers, harmonic frequency calculations of the optimized structures, and a number of properties such as electron densities at the bond critical points, orbital interaction energies, binding energies of the C–H···Y bound complexes are also summarized for better understanding of this type of H-bond. Not only the spectroscopic shift in C–H stretching frequency, but also the role of C–H···O H-bonds in microsolvation of several organic molecules has been highlighted. It has been found that depending upon activation of C–H moiety, C–H···Y H-bonds can provide primary or secondary stabilization for the growth of the primary solvation shell around organic molecules.

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Reprinted with permission from Ref.75. Copyright © 2014 WILEY–VCH Verlag GmbH & Co. KGaA, Weinheim.

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Reference92—reproduced by permission of the PCCP Owner Societies.

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Reference95—reproduced by permission of the PCCP Owner Societies.

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Reference95—reproduced by permission of the PCCP Owner Societies.

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Reference95—reproduced by permission of the PCCP Owner Societies.

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Adapted with permission from Ref.39. Copyright © 2019 American Chemical Society.

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Reprinted with permission from Ref.39. Copyright © 2019 American Chemical Society.

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Acknowledgements

SJW would like to acknowledge the exemplary hard work and dedication shown by his students Drs. Pranav Shirhatti, Aditi Bhattacherjee, and Sanat Ghosh whose work is presented in the review. The technical support provided by Mr Ajay Patil and Mr Sachin Temkar is also gratefully acknowledged. The work was supported by the Tata Institute of Fundamental Research, Mumbai via project no. 12-R&D-TFR-5.10-0100.

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  1. Sanat Ghosh

    Present address: Universidad Complutense de Madrid, Madrid, Spain

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  1. Department of Chemical Sciences, Tata Institute of Fundamental Research, Homi Bhabha Road, Mumbai, 400 005, India

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Ghosh, S., Wategaonkar, S. C–H···Y (Y=N, O, π) Hydrogen Bond: A Unique Unconventional Hydrogen Bond. J Indian Inst Sci 100, 101–125 (2020). https://doi.org/10.1007/s41745-019-00145-5

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