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Interconverting Hydrogen-Bonding and Weak n → π* Interactions in Aqueous Solution: A Direct Spectroscopic Evidence

  • Pranab Deb
    Pranab Deb
    Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India
    Academy of Scientific & Innovative Research (AcSIR), CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India
    More by Pranab Deb
  • Geun Young Jin
    Geun Young Jin
    Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan 44919, Republic of Korea
    Department of NanoFusion Technology, Pusan National University, Busan 46241, Republic of Korea
  • Santosh K. Singh
    Santosh K. Singh
    Department of Chemistry, Indian Institute of Science Education and Research (IISER), Dr. Homi Bhabha Road, Pune 411008, India
  • Juran Moon
    Juran Moon
    Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan 44919, Republic of Korea
    More by Juran Moon
  • Hyejin Kwon
    Hyejin Kwon
    Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan 44919, Republic of Korea
    More by Hyejin Kwon
  • Aloke Das*
    Aloke Das
    Department of Chemistry, Indian Institute of Science Education and Research (IISER), Dr. Homi Bhabha Road, Pune 411008, India
    *A.D.: E-mail: [email protected]. Tel: +91-20-25908078.
    More by Aloke Das
  • Sayan Bagchi*
    Sayan Bagchi
    Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India
    Academy of Scientific & Innovative Research (AcSIR), CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India
    *S.B.: E-mail: [email protected]. Tel: +91-20-25903048.
    More by Sayan Bagchi
  • , and 
  • Yung Sam Kim*
    Yung Sam Kim
    Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan 44919, Republic of Korea
    *Y.S.K.: E-mail: [email protected]. Tel: +82-52-217-2530.
    More by Yung Sam Kim
Cite this: J. Phys. Chem. Lett. 2018, 9, 18, 5425–5429
Publication Date (Web):August 27, 2018
https://doi.org/10.1021/acs.jpclett.8b02398
Copyright © 2018 American Chemical Society

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    Abstract

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    Molecular structure and function depend on myriad noncovalent interactions. However, the weak and transient nature of noncovalent interactions in solution makes them challenging to study. Information on weak interactions is typically derived from theory and indirect structural data. Solvent fluctuations, not revealed by structure analysis, further complicate the study of these interactions. Using 2D infrared spectroscopy, we show that the strong hydrogen bond and the weak n → π* interaction coexist and interconvert in aqueous solution. We found that the kinetics of these interconverting interactions becomes faster with increasing water content. This experimental observation provides a new perspective on the existence of weak noncovalent interactions in aqueous solution.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jpclett.8b02398.

    • Materials, DFT calculations, spectroscopic details, molecular dynamics simulations, Figures S1–S21, and Tables S1–S13 (PDF)

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    Cited By

    This article is cited by 17 publications.

    1. Prakash Panwaria, Aloke Das. Modulation of n → π* Interaction in the Complexes of p-Substituted Pyridines with Aldehydes: A Theoretical Study. The Journal of Physical Chemistry A 2023, 127 (29) , 6081-6090. https://doi.org/10.1021/acs.jpca.3c03103
    2. Chaowei Yin, Hanwei Lu, Hebo Ye, Zelin Feng, Hanxun Zou, Meilan Zhang, Lei You. Double n→π* Interactions with One Electron Donor: Structural and Mechanistic Insights. Organic Letters 2023, 25 (9) , 1470-1475. https://doi.org/10.1021/acs.orglett.3c00205
    3. Deborin Ghosh, Sushil S. Sakpal, Srijan Chatterjee, Samadhan H. Deshmukh, Hyejin Kwon, Yung Sam Kim, Sayan Bagchi. Association–Dissociation Dynamics of Ionic Electrolytes in Low Dielectric Medium. The Journal of Physical Chemistry B 2022, 126 (1) , 239-248. https://doi.org/10.1021/acs.jpcb.1c08613
    4. Gary W. Breton, Lindsey O. Davis, Kenneth L. Martin, Thomas A. Chambers. A Search for X-ray Crystallographic Evidence of n → π* Interactions in a Series of Substituted 2-(Dimethylamino)biphenyl-2′-carboxaldehydes. Crystal Growth & Design 2019, 19 (7) , 3895-3904. https://doi.org/10.1021/acs.cgd.9b00322
    5. B. Suryaprasad, Swaroop Chandra, N. Ramanathan, K. Sundararajan. Collective stabilization through n→π* and P…π phosphorous bonding with cooperative halogen and hydrogen bonding in POCl3-Nitrile dimers: Matrix isolation infrared spectroscopic and ab initio computational studies. Journal of Molecular Structure 2023, 1278 , 134916. https://doi.org/10.1016/j.molstruc.2023.134916
    6. Youngjae Cho, Junhwan Bae, Mi-Jung Choi. Physicochemical Characteristics of Meat Analogs Supplemented with Vegetable Oils. Foods 2023, 12 (2) , 312. https://doi.org/10.3390/foods12020312
    7. Prakash Panwaria, Marcos Juanes, Kamal K. Mishra, Rizalina Saragi, Kshetrimayum Borish, Imanol Usabiaga, Ander Camiruaga, José A. Fernández, Alberto Lesarri, Aloke Das. Microhydration of Phenyl Formate: Gas‐Phase Laser Spectroscopy, Microwave Spectroscopy, and Quantum Chemistry Calculations. ChemPhysChem 2022, 23 (24) https://doi.org/10.1002/cphc.202200330
    8. Juhi Dutta, Chinmay Routray, Shalini Pandey, Himansu S. Biswal. Intermolecular noncovalent interactions with carbon in solution. Chemical Science 2022, 13 (48) , 14327-14335. https://doi.org/10.1039/D2SC05431K
    9. Prakash Panwaria, Aloke Das. Understanding the n → π* non-covalent interaction using different experimental and theoretical approaches. Physical Chemistry Chemical Physics 2022, 24 (37) , 22371-22389. https://doi.org/10.1039/D2CP02070J
    10. Subhrakant Jena, Juhi Dutta, Kiran Devi Tulsiyan, Akshay Kumar Sahu, Shubhranshu Shekhar Choudhury, Himansu S. Biswal. Noncovalent interactions in proteins and nucleic acids: beyond hydrogen bonding and π-stacking. Chemical Society Reviews 2022, 51 (11) , 4261-4286. https://doi.org/10.1039/D2CS00133K
    11. Jayashree Nagesh. Cross-Talk between Overlap Interactions in Biomolecules: A Case Study of the β-Turn Motif. Molecules 2021, 26 (6) , 1533. https://doi.org/10.3390/molecules26061533
    12. Deborin Ghosh, Samadhan Deshmukh, Srijan Chatterjee, Sushil Sakpal, Tapas Haldar, Ambuj Dhakad, Somnath Kashid, Sayan Bagchi. Two Dimensional Infrared Spectroscopy: A Structure Sensitive Technique with Ultrafast Time Resolution. 2021, 39-56. https://doi.org/10.1007/978-981-33-6084-6_2
    13. Prakash Panwaria, Aloke Das. Exploring Non-covalent Interactions by Jet-Cooled Electronic and Vibrational Spectroscopy. 2021, 57-86. https://doi.org/10.1007/978-981-33-6084-6_3
    14. Biswajit Sahariah, Bani Kanta Sarma. Spectroscopic evidence of n → π* interactions involving carbonyl groups. Physical Chemistry Chemical Physics 2020, 22 (46) , 26669-26681. https://doi.org/10.1039/D0CP03557B
    15. Bhavesh Khatri, Puja Majumder, Jayashree Nagesh, Aravind Penmatsa, Jayanta Chatterjee. Increasing protein stability by engineering the n → π* interaction at the β-turn. Chemical Science 2020, 11 (35) , 9480-9487. https://doi.org/10.1039/D0SC03060K
    16. Shubhra Sarkar, N. Ramanathan, P.K. Sruthi, K. Sundararajan. Computational and experimental evidence of N–H…π and cooperative πN…π∗ interactions in pyrrole…benzene and pyrrole…ethylene heterodimers at low temperatures. Journal of Molecular Structure 2020, 1209 , 127983. https://doi.org/10.1016/j.molstruc.2020.127983
    17. Nicole A. Wenzell, Himal K. Ganguly, Anil K. Pandey, Megh R. Bhatt, Glenn P. A. Yap, Neal J. Zondlo. Electronic and Steric Control of n→π* Interactions: Stabilization of the α‐Helix Conformation without a Hydrogen Bond. ChemBioChem 2019, 20 (7) , 963-967. https://doi.org/10.1002/cbic.201800785

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