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Hydrogen Bonding 12/11/10 10:16 PM

Hydrogen Bonding
Hydrogen bonding is a special type of dipole-dipole attraction between molecules, not a covalent bond to a
hydrogen atom. It results from the attractive force between a hydrogen atom covalently bonded to a very
electronegative atom such as a N, O, or F atom and another very electronegative atom. Hydrogen bond strengths
range from 4 kJ to 50 kJ per mole of hydrogen bonds.

In molecules containing N-H, O-H or F-H bonds, the large difference in electronegativity between the H
atom and the N, O or F atom leads to a highly polar covalent bond (i.e., a bond dipole). The
electronegativities are listed below.

element electronegativity value

H 2.1

N 3.0

O 3.5

F 4.1

Because of the difference in electronegativity, the H atom bears a large partial positive charge and the N,
O or F atom bears a large partial negative charge.

A H atom in one molecule is electrostatically attracted to the N, O, or F atom in another molecule.

=O

Missing Plug-in Missing Plug-in =N

=H

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Hydrogen Bonding 12/11/10 10:16 PM

Hydrogen bonding between two Hydrogen bonding between a


water (H2 O) molecules. Note water molecule and an ammonia
that the O atom in one molecule (NH 3 ) molecule. Note that the
is attracted to a H atom in the N atom in the NH 3 molecule is
second molecule. attracted to a H atom in the
H2 O molecule.

Physical Consequences of Hydrogen Bonding

At 25o C, nitrosyl fluoride (ONF) is a gas whereas water is a liquid. Why?


ONF and water have about the same shape.
ONF has a higher molecular weight (49 amu) than water (18 amu).
Conclusion: London dispersion forces not responsible for the difference between these two
compounds.
ONF and water have the same dipole moment.
Conclusion: dipole-dipole forces not responsible for the difference between these two compounds.
ONF cannot form hydrogen bonds; water can form hydrogen bonds.

=O

=F
Missing Plug-in Missing Plug-in
=N

=H

The structure of ONF. The structure of H2 O.

Microscopic view of ONF at Microscopic view of H2 O at


25o C. 25o C.

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