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How to find the strongest hydrogen in a molecule? What to look for? What are the main rules?

How to find the strongest hydrogen in a molecule? What to look for? What are the main rules?

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A Hydrogen bonding exists when a hydrogen atom is bonded to two or more other atoms, a donor atom X and an acceotor atom Y. Since the hydrogen atom has only one orbital at sufficiently low energy, hydrogen bonds are mainly electrostatic in natur,but covalent and repulsive orbital-orbital interaction are also present.

The strength of hydrogen bond is governed by,

  • the inherent hydrogen bond donor strength (acidity) of the hydrogen atom and the acceptor capability of the respective acceptor group.
  • collective effects as cooperative,competitive, synergetic effects which increase or decrease the inherent donor strength and acceptor capabilities.
  • structural features as the number of acceptor groups,the hydrogen bond angles build by the acceptors, donor etc.
  • packing effects and constraints of respective crystal structure.
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