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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Matter: Pure Substances and Mixtures
According to its composition, the matter can be classified into two broad categories — pure substances and mixtures. 
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The vibrational frequency of a bond is directly proportional to its bond strength. As a result, stronger bonds vibrate at higher frequencies, while weaker bonds vibrate at lower frequencies. The stretching vibration of the strong O–H bond in alcohols and phenols (very dilute solution or gas phase) appears as a sharp peak at 3600–3650 cm−1.
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Model molecules to classify CHO hydrogen-bonds.

Amol M Vibhute1, U Deva Priyakumar, Arthi Ravi

  • 1School of Chemistry, Indian Institute of Science Education and Research (IISER), Thiruvananthapuram, Kerala-695551, India. kms@iisertvm.ac.in.

Chemical Communications (Cambridge, England)
|April 20, 2018
PubMed
Summary
This summary is machine-generated.

Researchers created locked molecules forming single hydrogen bonds. The NMR signal shift correlated with oxygen hybridization and hydrogen bond strength, offering insights into molecular interactions.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • Hydrogen bonds play a crucial role in molecular structure and function.
  • Understanding the factors influencing hydrogen bond strength is essential for chemical and biological processes.
  • Conformationally locked molecules provide a unique platform to study specific interactions in isolation.

Purpose of the Study:

  • To develop conformationally locked molecules capable of forming a single hydrogen bond.
  • To investigate the relationship between electron density at the acceptor atom and hydrogen bond characteristics.
  • To correlate NMR chemical shifts with computational measures of hydrogen bond strength.

Main Methods:

  • Synthesis of conformationally locked molecular systems.
  • Nuclear Magnetic Resonance (NMR) spectroscopy (1H NMR) to observe chemical shifts.
  • Computational chemistry methods to quantify hydrogen bond strengths and analyze electronic properties.

Main Results:

  • A series of conformationally locked molecules were successfully synthesized, each forming a single CHO hydrogen bond.
  • The 1H NMR signals for the hydrogen involved in the CHO H-bond exhibited downfield shifts ranging from 0.93 to 1.6 ppm.
  • The magnitude of the NMR chemical shift (Δδ) showed a strong correlation with the hybridization state of the acceptor oxygen atom.
  • Δδ also correlated with the hydrogen bond strengths as determined by computational analysis.

Conclusions:

  • The study demonstrates a clear correlation between NMR chemical shifts and the strength of CHO hydrogen bonds in conformationally locked systems.
  • The hybridization state of the acceptor oxygen atom is a significant factor influencing the observed NMR chemical shift.
  • These findings provide valuable insights into the nature of hydrogen bonding and offer a method for quantifying bond strengths using NMR spectroscopy.