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Aromatic rings act as hydrogen bond acceptors.

M Levitt¹, M F Perutz

¹MRC Laboratory of Molecular Biology, Cambridge, England.

Journal of Molecular Biology

|June 20, 1988

Summary

A novel aromatic hydrogen bond interaction between NH groups and benzene rings offers significant molecular stabilization. This interaction, crucial for molecular associations, is driven by partial atomic charges, not delocalized electrons.

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Area of Science:

Chemistry
Biochemistry
Molecular Biology

Background:

Hydrogen bonds are crucial for molecular interactions.
Aromatic rings, like benzene, are common in biological molecules.
The role of aromatic rings in hydrogen bonding was not fully understood.

Purpose of the Study:

To investigate the interaction between hydrogen bond donors and the center of benzene rings.
To quantify the strength and nature of this aromatic hydrogen bond.
To understand the implications for molecular associations.

Main Methods:

Simple energy calculations were performed.
Analysis focused on partial charges on ring atoms.
Comparison with known hydrogen bond strengths.

Main Results:

A significant interaction, termed aromatic hydrogen bond, was identified.
This bond contributes approximately 3 kcal/mol of stabilizing enthalpy.
The interaction strength is about half that of a normal hydrogen bond.
The interaction arises from partial charges on carbon and hydrogen atoms, not delocalized electrons.

Conclusions:

Aromatic hydrogen bonds are a significant force in molecular associations.
Understanding these bonds is crucial for fields like drug design.
Partial atomic charges play a key role in this interaction.

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