What Is the Chemical Structure of 2 5-Furandicarboxylic Acid

You encounter 2 5-Furandicarboxylic acid as a molecule with the formula C6H4O5. Its structure features a planar furan ring carrying carboxylic acid groups at positions 2 and 5.

• This compound serves as a sustainable alternative in polymer production and advanced materials, with commercial demand rising in recent chemical databases.

2 5-Furandicarboxylic Acid Molecular Structure

Furan Ring Backbone

When you examine the backbone of 2 5-Furandicarboxylic acid, you find a five-membered furan ring at its core. This ring contains four carbon atoms and one oxygen atom, forming a nearly planar structure. The planarity of the furan ring supports aromatic stability, which means the molecule maintains a strong π-electron system. This electronic arrangement helps stabilize the molecule and influences its chemical behavior.

The furan ring in 2 5-Furandicarboxylic acid shows minimal deviation from planarity. The C-O-C bond angle measures about 106-107°, shaping the ring geometry and electronic environment. This near-planar geometry preserves aromatic character and allows for effective π-π interactions, which contribute to the overall stability of the molecule.

You notice that the backbone does not flip as easily as a benzene ring. The carbonyl groups at positions 2 and 5 introduce asymmetry and non-linearity, which suppress ring-flipping and increase the stiffness of the backbone. In crystalline materials, the backbone often adopts a zig-zag conformation, while in amorphous domains, a helical shape is more common. These conformational preferences affect the physical properties of polymers made from 2 5-Furandicarboxylic acid.

Carboxylic Acid Groups at Positions 2 and 5

You see two carboxylic acid groups attached to the furan ring at the 2 and 5 positions. These groups play a crucial role in the molecule’s reactivity and ability to form hydrogen bonds. The carboxylic acid groups introduce polarity and allow for strong intermolecular interactions, which stabilize the crystalline structure.

• X-ray crystallography reveals that these carboxylic acid groups participate in hydrogen bonding, helping to stabilize the crystal lattice. For example, a hydrogen bond distance of about 2.06 Å between a carbonyl oxygen and a hydrogen on the furan ring supports the proposed molecular structure.
• Computational modeling and vibrational spectroscopy confirm that the most stable conformation involves both carboxylic acid groups in a syn–syn arrangement. This conformation enhances hydrogen bonding and further stabilizes the molecule.

You find that the presence of these groups makes 2 5-Furandicarboxylic acid highly reactive and suitable for polymerization. This property is essential for its use in sustainable materials, such as polyethylene furanoate (PEF), which offers superior barrier and mechanical properties compared to traditional plastics.

Atom Arrangement and Molecular Formula

The molecular formula C6H4O5 tells you that the molecule contains six carbon atoms, four hydrogen atoms, and five oxygen atoms. Here’s how these atoms arrange themselves:

• The furan ring provides four carbon atoms and one oxygen atom.
• Two carboxylic acid groups (–COOH) attach at the 2 and 5 positions, each contributing one carbon and two oxygen atoms.
• The four hydrogen atoms come from the furan ring and the carboxylic acid groups.

You can visualize the atom arrangement as follows:

• The furan ring sits at the center, with carboxylic acid groups branching off at opposite sides (positions 2 and 5).

• The SMILES notation (C1=C(OC(=C1)C(=O)O)C(=O)O) and InChI string confirm the exact connectivity of atoms.

• The molecular formula C6H4O5 corresponds to 2 5-Furandicarboxylic acid.

• The molecule contains a furan ring, which is a five-membered ring with one oxygen atom.

• Two carboxylic acid groups (–COOH) are attached at the 2 and 5 positions of the furan ring.

• The Lewis structure visualization shows the furan ring with two carboxylic acid groups attached at positions 2 and 5, matching the molecular formula.

You find that X-ray crystallography and computational modeling validate this arrangement, confirming the presence and orientation of carboxylic acid groups and the overall molecular framework. These techniques also reveal how hydrogen bonding and molecular geometry stabilize the crystalline phase.

2 5-Furandicarboxylic Acid Functional Groups and Chemical Properties

Carboxylic Acid Functional Groups

You find that the most defining feature of 2 5-Furandicarboxylic acid lies in its two carboxylic acid groups. These groups attach at the 2 and 5 positions of the furan ring. Each carboxylic acid group consists of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group. This arrangement gives the molecule its acidic character.

The carboxylic acid groups play a major role in hydrogen bonding. You observe that these groups form strong intermolecular hydrogen bonds with neighboring molecules. This network of hydrogen bonds leads to a very high melting point, which exceeds 310°C, and makes the compound insoluble in most common solvents. The hydrogen bonding stabilizes the solid structure and affects how the molecule behaves in different environments.

You can estimate the acidity of these groups by looking at similar compounds. For example, the pKa value for a related molecule, 5-Hydroxymethyl-furan-2-carboxylic acid, is about 3.11. This value suggests that the carboxylic acid groups in 2 5-Furandicarboxylic acid also show strong acidity, making them reactive in chemical processes such as polymerization.

Note: The strong hydrogen bonding and acidity of the carboxylic acid groups make this molecule a valuable building block for high-performance polymers and sustainable materials.

Influence of Structure on Chemical Properties

The unique structure of 2 5-Furandicarboxylic acid shapes its chemical and physical properties. The combination of a rigid furan ring and two carboxylic acid groups gives the molecule high thermal stability and low solubility in water and organic solvents. You can see these properties in the following table:

You notice that the molecule’s rigidity and hydrogen bonding network contribute to its high melting point and limited solubility. These features make it suitable for applications that require heat resistance and durability.

The chemical structure also influences the environmental impact of the compound. You benefit from its bio-based origin and excellent biodegradability. Microorganisms can break down the molecule, which helps reduce long-term pollution. The production process uses renewable resources, lowering greenhouse gas emissions compared to traditional petrochemical methods. You find that the molecule’s superior barrier properties and heat resistance make it ideal for food packaging and beverage bottles. It also acts as a plasticizer, improving flexibility and processability in plastics while maintaining low toxicity.

• FDCA is a natural organic acid with excellent biodegradability.
• Its production uses renewable resources, reducing greenhouse gas emissions.
• FDCA-based bioplastics reduce plastic waste and carbon footprint.
• The molecule provides high thermal stability and superior mechanical properties.
• FDCA-based polymers are compatible with other monomers, supporting sustainable material production.

Recent advancements in synthesis focus on catalytic conversion from furfural, a biomass-derived material. Researchers have developed efficient and green catalysts that improve yield and purity. These methods align with green chemistry principles and support sustainable development. You see that these innovations make the production of 2 5-Furandicarboxylic acid more environmentally friendly and economically feasible.

The unique structure of this molecule allows it to serve as a precursor for dyes and polymers with enhanced light and heat resistance. Its bio-based and biodegradable nature ensures that products made from it are safer for the environment, especially in sensitive applications like food packaging and cosmetics.

2 5-Furandicarboxylic Acid Chemical Identifiers

CAS Number

You can identify 2 5-Furandicarboxylic acid using its official CAS number. The Chemical Abstracts Service (CAS) assigns a unique number to every chemical substance. This number helps you find reliable information in scientific literature and product catalogs.

• The official CAS number for 2 5-Furandicarboxylic acid is 3238-40-2.
• You will see this number listed on chemical supplier websites and in multiple language versions of product pages.
• The repeated use of this CAS number across databases confirms its accuracy and official recognition.

Tip: When searching for safety data sheets or regulatory documents, always use the CAS number for precise results.

SMILES Notation

SMILES (Simplified Molecular Input Line Entry System) notation gives you a way to represent the structure of a molecule using a line of text. This format allows you to enter chemical structures into databases or modeling software quickly. For 2 5-Furandicarboxylic acid, the SMILES notation is:

C1=C(OC(=C1)C(=O)O)C(=O)O

You can use this code to search chemical databases or to draw the molecule in digital tools. SMILES notation helps you share and analyze chemical structures efficiently.

InChI and InChIKey

You will often see InChI (International Chemical Identifier) and InChIKey used in scientific research and chemical databases. These identifiers provide a standardized way to describe a molecule’s structure and ensure you can find the same compound across different platforms.

• The InChI string encodes the exact molecular structure.
• The InChIKey is a short, fixed-length code derived from the InChI string.
• You can use the InChIKey to search for 2 5-Furandicarboxylic acid in databases like PubChem and ChEBI.
• These identifiers allow you to cross-reference information, link to patents, and ensure you access consistent data.
• The InChIKey connects you to authoritative sources and supports accurate chemical analysis.

Note: InChI and InChIKey make it easy for you to retrieve and share chemical information across different scientific resources.

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You see that 2 5-Furandicarboxylic acid features a rigid furan ring with two carboxylic acid groups. This unique structure shapes its chemical properties and makes it valuable for sustainable polymer production.

Unlike other dicarboxylic acids, its furan ring gives polymers improved strength and barrier properties, helping you create eco-friendly materials.

FAQ

What is the main use of 2 5-Furandicarboxylic acid?

You use 2 5-Furandicarboxylic acid mainly to produce bio-based polymers like polyethylene furanoate (PEF), which replaces traditional plastics in packaging and bottles.

Is 2 5-Furandicarboxylic acid safe to handle?

You should handle this compound with care. It may cause skin or eye irritation. Always wear gloves and safety goggles in the laboratory.

How does the structure affect its properties?

You benefit from the rigid furan ring and carboxylic acid groups. These features give the molecule high thermal stability and strong hydrogen bonding.

Tip: Always check the safety data sheet before working with any chemical.