Can 2 - Thiopheneethanol form hydrogen bonds?

As a reliable supplier of 2 - Thiopheneethanol, I often encounter various inquiries from customers interested in its chemical properties. One common question that frequently arises is whether 2 - Thiopheneethanol can form hydrogen bonds. In this blog post, I will delve into the scientific aspects of this query and provide a comprehensive answer.

Understanding Hydrogen Bonds

Before we explore the potential of 2 - Thiopheneethanol to form hydrogen bonds, it's essential to understand what hydrogen bonds are. A hydrogen bond is a special type of intermolecular force that occurs when a hydrogen atom is covalently bonded to a highly electronegative atom (such as nitrogen, oxygen, or fluorine) and is attracted to another electronegative atom in a different molecule. This interaction results in a relatively strong, yet non - covalent, bond between the molecules. Hydrogen bonds play a crucial role in many biological and chemical processes, such as the structure of DNA, the solubility of compounds in water, and the physical properties of substances like boiling and melting points.

Structure of 2 - Thiopheneethanol

The chemical formula of 2 - Thiopheneethanol is C₆H₈OS. Its structure consists of a thiophene ring, which is a five - membered heterocyclic ring containing four carbon atoms and one sulfur atom, and an ethanol group (-CH₂CH₂OH) attached to the thiophene ring. The presence of the hydroxyl group (-OH) in the ethanol moiety is a key factor when considering the possibility of hydrogen bond formation.

Conditions for Hydrogen Bond Formation

For a molecule to form hydrogen bonds, it must meet two main conditions:

It must have a hydrogen atom covalently bonded to a highly electronegative atom (usually N, O, or F).
There must be an electronegative atom (N, O, or F) in another molecule with a lone pair of electrons that can interact with the hydrogen atom.

In the case of 2 - Thiopheneethanol, the hydroxyl group (-OH) has a hydrogen atom covalently bonded to an oxygen atom. Oxygen is a highly electronegative atom, with an electronegativity value of 3.44 on the Pauling scale. This creates a polar covalent bond between the hydrogen and oxygen atoms, where the oxygen atom has a partial negative charge (δ⁻) and the hydrogen atom has a partial positive charge (δ⁺).

Hydrogen Bonding in 2 - Thiopheneethanol

2 - Thiopheneethanol can form hydrogen bonds in two main ways:

Intramolecular hydrogen bonding: Although less likely in 2 - Thiopheneethanol due to the relatively large distance between the hydroxyl group and the sulfur atom in the thiophene ring, in theory, if the molecule adopts a suitable conformation, there could be a weak intramolecular interaction between the hydrogen of the hydroxyl group and the sulfur atom. However, sulfur is less electronegative than oxygen, and the strength of such an interaction would be much weaker compared to a typical hydrogen bond with N, O, or F.
Intermolecular hydrogen bonding: This is the more significant form of hydrogen bonding in 2 - Thiopheneethanol. The hydrogen atom of the hydroxyl group in one 2 - Thiopheneethanol molecule can form a hydrogen bond with the lone pair of electrons on the oxygen atom of another 2 - Thiopheneethanol molecule. This intermolecular hydrogen bonding leads to the association of multiple 2 - Thiopheneethanol molecules, which in turn affects its physical properties. For example, compared to similar non - hydrogen - bonding compounds of similar molecular weight, 2 - Thiopheneethanol has a relatively higher boiling point because more energy is required to break these intermolecular hydrogen bonds during the phase transition from liquid to gas.

Impact on Physical and Chemical Properties

The ability of 2 - Thiopheneethanol to form hydrogen bonds has several implications for its physical and chemical properties:

Solubility: Hydrogen bonding allows 2 - Thiopheneethanol to dissolve in polar solvents such as water. The hydroxyl group can form hydrogen bonds with water molecules, which helps to overcome the intermolecular forces between 2 - Thiopheneethanol molecules and disperse them in the water solvent.
Boiling and melting points: As mentioned earlier, intermolecular hydrogen bonding increases the boiling point of 2 - Thiopheneethanol. The molecules are held together more tightly due to these hydrogen bonds, and a larger amount of energy is needed to separate them and convert the liquid into a gas. Similarly, the melting point is also affected, as the hydrogen bonds need to be disrupted for the solid to turn into a liquid.
Reactivity: Hydrogen bonding can influence the reactivity of 2 - Thiopheneethanol in chemical reactions. The partial positive charge on the hydrogen atom of the hydroxyl group can make it more susceptible to attack by nucleophiles, and the hydrogen - bonded environment can also affect the orientation and availability of the reactive sites on the molecule.

Comparison with Other Compounds

To better understand the significance of hydrogen bonding in 2 - Thiopheneethanol, let's compare it with some other related compounds.

4 - Nitroaniline

4 - Nitroaniline is another compound that can form hydrogen bonds. It has an amino group (-NH₂) and a nitro group (-NO₂). The hydrogen atoms in the amino group can form hydrogen bonds with the oxygen atoms of the nitro group in other molecules or with other polar molecules. Similar to 2 - Thiopheneethanol, the hydrogen bonding in 4 - Nitroaniline affects its solubility, boiling point, and reactivity.

Imidazole - 1 - ethanol Antifungal Agent

Imidazole - 1 - ethanol Antifungal Agent also contains a hydroxyl group and a heterocyclic ring. The hydroxyl group can participate in hydrogen bonding, which is important for its biological activity. Hydrogen bonding can help the molecule interact with target proteins or receptors in the fungus, facilitating its antifungal action.

High - purity Cyclohexanecarbonyl Chloride

High - purity Cyclohexanecarbonyl Chloride does not have a hydrogen atom bonded to a highly electronegative atom (N, O, or F) in a way that can form typical hydrogen bonds. As a result, its physical properties such as boiling point and solubility are different from those of 2 - Thiopheneethanol. It has a lower boiling point compared to 2 - Thiopheneethanol of similar molecular weight because it lacks the strong intermolecular hydrogen bonding forces.

Applications and Significance

The ability of 2 - Thiopheneethanol to form hydrogen bonds makes it useful in various applications:

Pharmaceutical industry: Hydrogen bonding can influence the drug - receptor interactions. 2 - Thiopheneethanol can be used as an intermediate in the synthesis of pharmaceutical compounds. Its hydrogen - bonding properties can help the final drug molecule bind more effectively to its target in the body.
Flavor and fragrance industry: The intermolecular forces due to hydrogen bonding can affect the volatility and odor characteristics of 2 - Thiopheneethanol. It can be used as a flavoring agent or in the formulation of fragrances, where its ability to interact with other molecules through hydrogen bonding contributes to the overall sensory properties.

Conclusion

In conclusion, 2 - Thiopheneethanol can form intermolecular hydrogen bonds through the hydroxyl group in its structure. These hydrogen bonds have a significant impact on its physical and chemical properties, as well as its applications in different industries. If you are interested in purchasing high - quality 2 - Thiopheneethanol for your specific needs, feel free to contact us for further details and to start a procurement negotiation. We are committed to providing you with the best products and services.

References

Atkins, P., & de Paula, J. (2014). Physical Chemistry. Oxford University Press.
Morrison, R. T., & Boyd, R. N. (2002). Organic Chemistry. Prentice Hall.