9.2 intramolecular hydrogen bonding with example

intramolecular hydrogen bonding

Intramolecular Hydrogen Bonding: Unveiling the Hidden Forces Within Molecules

Chemistry is a fascinating world filled with intricate interactions between atoms and molecules. One such captivating phenomenon is intramolecular hydrogen bonding. Unlike its well-known counterpart, intermolecular hydrogen bonding, which occurs between different molecules, intramolecular hydrogen bonding takes place within a single molecule. This unique bonding mechanism plays a crucial role in the properties, structure, and behavior of various compounds. In this article, we will delve into the captivating world of intramolecular hydrogen bonding, exploring its significance and shedding light on its diverse manifestations.

To understand intramolecular kind of hydrogen bonding, let us first revisit the basics of hydrogen bonding itself. Hydrogen bonding is a special type of intermolecular force that arises when a hydrogen atom, covalently bonded to an electronegative atom (such as oxygen, nitrogen, or fluorine), interacts with another electronegative atom in a different molecule. This interaction leads to the formation of a weak bond, which, despite its relative weakness, can significantly influence the physical and chemical properties of substances.

Intramolecular hydrogen bonding occurs when a molecule contains two or more hydrogen bond donor and acceptor sites within its structure. The hydrogen atoms in the molecule form bonds with electronegative atoms, such as oxygen or nitrogen, located within the same molecule. This creates a loop-like structure within the molecule, where the hydrogen atom acts as a bridge between the donor and acceptor sites. The strength and stability of intramolecular hydrogen bonding can vary depending on factors such as the nature of the atoms involved, their proximity, and the surrounding environment.

One of the key implications of intramolecular hydrogen bonding is its effect on molecular conformation. In molecules with intramolecular hydrogen bonds, the bond formation leads to a preferred orientation of the participating groups, which affects the overall shape and geometry of the molecule. This conformational influence plays a pivotal role in determining the molecule’s physical properties, such as boiling point, melting point, and solubility. For example, intramolecular hydrogen bonding in some organic compounds can result in increased boiling points due to the additional intermolecular forces involved.

Moreover, intramolecular hydrogen bonding can significantly impact chemical reactivity. The presence of intramolecular hydrogen bonds can influence the accessibility of functional groups within a molecule, affecting its susceptibility to various chemical reactions. In some cases, the hydrogen bond can enhance or hinder the reactivity of certain functional groups, leading to interesting phenomena such as tautomerism. Tautomers are isomeric forms of a compound that readily interconvert by relocating a hydrogen atom via intramolecular hydrogen bonding, thereby altering the distribution of electron density and functional groups.

Intramolecular hydrogen bonding is not limited to organic compounds; it also plays a significant role in biological systems. For instance, in proteins, intramolecular hydrogen bonding helps stabilize the secondary structures, such as alpha helices and beta sheets, which are vital for the protein’s overall stability and functionality. Additionally, nucleic acids, such as DNA and RNA, rely on intramolecular hydrogen bonding to maintain their characteristic double-helical structures.

intramolecular hydrogen bonding 1

The study of intramolecular hydrogen bonding is a complex and interdisciplinary field that combines principles from organic chemistry, physical chemistry, and molecular biology. Researchers employ various experimental and computational techniques to investigate the presence and effects of intramolecular hydrogen bonding in different compounds. Techniques such as X-ray crystallography, nuclear magnetic resonance (NMR) spectroscopy, and computational modeling provide valuable insights into the structural aspects and energetics of intramolecular hydrogen bonding.

People Also Asked

What is the difference between intermolecular and intramolecular hydrogen bonding?

Intermolecular hydrogen bonding occurs between different molecules, where a hydrogen atom in one molecule interacts with an electronegative atom in a different molecule. This bonding occurs between neighboring molecules and contributes to the overall properties of the substance.

On the other hand, intramolecular hydrogen bonding takes place within a single molecule. In this case, the hydrogen atom is bonded to an electronegative atom within the same molecule, forming a bridge between the donor and acceptor sites. This bonding occurs within the molecular structure and influences the conformation, reactivity, and properties of the molecule itself.

What are two examples of intramolecular hydrogen bonding?

There are numerous examples of intramolecular kind of hydrogen bonding across different compounds. Two common examples are:

a) Ethanol (CH3CH2OH): In ethanol, intramolecular kind of hydrogen bonding occurs between the hydrogen atom of the hydroxyl group (-OH) and the oxygen atom of the carbonyl group (-C=O). This interaction leads to the formation of a stable five-membered ring within the molecule.

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b) 2-Aminobenzamide (C7H8N2O): In this compound, intramolecular kind of hydrogen bonding occurs between the hydrogen atom of the amino group (-NH2) and the oxygen atom of the carbonyl group (-C=O). The hydrogen bonding stabilizes the molecular conformation and influences the compound’s physical and chemical properties.

ch Triple bond

Is water an example of intramolecular hydrogen bonding?

No, water (H2O) is not an example of intramolecular kind of hydrogen bonding. Water exhibits intermolecular hydrogen bonding, where the hydrogen atoms of one water molecule form bonds with the oxygen atoms of neighboring water molecules. This intermolecular hydrogen bonding contributes to the unique properties of water, such as its high boiling point, surface tension, and solvent capabilities.

g intermolecular and intramolecular hydrogen bonding

Intermolecular Hydrogen BondingIntramolecular kind Hydrogen Bonding
DefinitionHydrogen bonding between different moleculesHydrogen bonding within a single molecule
Nature of InteractionWeak electrostatic interaction between hydrogen and electronegative atoms in different moleculesWeak electrostatic interaction between hydrogen and electronegative atoms within the same molecule
Type of Bonds FormedHydrogen atom of one molecule interacts with an electronegative atom of a different moleculeHydrogen atom within a molecule interacts with an electronegative atom in the same molecule
Influence on MoleculesDetermines physical and chemical properties of substancesAffects molecular conformation, reactivity, and properties
ExamplesHydrogen bonding between water moleculesIntramolecular hydrogen bonding in ethanol (CH3CH2OH)
Hydrogen bonding between ammonia (NH3) moleculesIntramolecular hydrogen bonding in 2-Aminobenzamide

Note: This table provides a general comparison between intermolecular and intramolecular hydrogen bonding. There are many more examples and variations of hydrogen bonding in different compounds and systems.

conclusion

Intramolecular kind of hydrogen bonding is a captivating phenomenon that goes beyond the traditional intermolecular interactions we commonly encounter. It adds an extra layer of complexity

to the behavior and properties of molecules, influencing their conformation, reactivity, and stability. From organic compounds to biological macromolecules, intramolecular hydrogen bonding plays a crucial role in shaping the world of chemistry. Exploring and understanding this hidden force opens up new avenues for designing molecules with desired properties and advancing our knowledge of the molecular world.

Read Also,

intramolecular hydrogen bonding vs intermolecular hydrogen bonding

hydrogen bond acceptor

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