C10h13no4

Introduction

C10H13NO4 denotes a molecular composition consisting of ten carbon atoms, thirteen hydrogen atoms, one nitrogen atom, and four oxygen atoms. This formula is shared by a diverse array of organic molecules, many of which contain aromatic systems and amide or ester functionalities. Compounds with this empirical formula appear in pharmaceuticals, agrochemicals, and specialty materials. Understanding the structural diversity, synthesis routes, and physical properties of C10H13NO4 is essential for chemists engaged in drug discovery, material design, and environmental assessment.

Molecular Formula and General Properties

Elemental Composition and Degrees of Unsaturation

The degree of unsaturation (double bond equivalents) for C10H13NO4 can be calculated using the formula:

(2C + 2 + N - H)/2
(2*10 + 2 + 1 - 13)/2
(20 + 2 + 1 - 13)/2 = 10/2 = 5

A value of five indicates the presence of five rings and/or double bonds. In practice, this often corresponds to a single aromatic benzene ring (four degrees) plus one carbonyl double bond (one degree), though other topologies such as lactams, cyclic ethers, or fused ring systems are possible.

Isotopic Patterns and Mass Spectrometry

In mass spectrometry, a molecule with the formula C10H13NO4 typically shows a molecular ion at m/z 211 for the protonated species [M+H]+. Natural isotopic abundance of carbon (12C and 13C) leads to a small M+1 peak, while nitrogen’s single isotope (14N) does not affect the pattern. The presence of four oxygen atoms can result in a characteristic fragmentation pattern where cleavage adjacent to the carbonyl yields a prominent ion at m/z 87, corresponding to the neutral loss of a C6H6O fragment.

Structural Isomerism

Aromatic Core Variants

Most C10H13NO4 molecules incorporate a benzene ring. Variations arise from the positions of heteroatom substituents (hydroxyl, amino, carboxyl, methoxy) and from side chains such as acetamide, acetyl, or methoxy groups. For example, an ortho-hydroxybenzoic acid derivative with an N-methylacetamide side chain fits the formula.

Non‑Aromatic Frameworks

Isomeric structures lacking an aromatic ring exist. For instance, a pyrrolidinyl lactone with an attached phenyl group or a cyclic imide fused to a cyclohexane ring can also satisfy the formula. These variants often exhibit different physicochemical properties, such as lower melting points and altered solubility profiles.

Conformational Isomerism

Even within a fixed connectivity, rotamers around amide bonds or stereoisomers at chiral centers can exist. For compounds containing a chiral center at the α‑carbon of an acyl group, enantiomeric pairs are typically formed, influencing biological activity and metabolic fate.

Functional Group Distribution

Amide Moieties

The presence of a nitrogen atom bonded to a carbonyl carbon defines an amide functionality. In C10H13NO4, the amide often appears as an N‑methyl or N‑ethyl substitution, which modulates lipophilicity and hydrogen‑bonding capacity. Amides contribute to the rigidity of the backbone and are commonly involved in key interactions with biological targets.

Ester and Acidic Groups

Four oxygen atoms allow for the inclusion of ester linkages or carboxylic acids. Esterification of a phenolic hydroxyl group with a methylene carboxylic acid yields a β‑ketoester motif. Alternatively, a free carboxylate group can be present, providing a site for salt formation and increasing aqueous solubility.

Phenolic Hydroxyls and Methoxy Substituents

Hydroxyl groups attached directly to the aromatic ring confer phenolic character, enabling hydrogen bonding and potential antioxidant activity. Methoxy groups, if present, add electron-donating effects, altering electronic density and affecting metabolic stability.

Synthesis and Methods of Preparation

Condensation Reactions

A common route to C10H13NO4 derivatives involves the condensation of a substituted benzaldehyde with a primary amine in the presence of a catalytic acid, forming an imine that can be hydrolyzed to an amide. Subsequent acylation with a chloroacetyl chloride introduces the additional carbonyl.

Reductive Amination

Reductive amination of an aromatic ketone with an amine and a reducing agent such as sodium cyanoborohydride yields an N‑alkylated amide while preserving the aromatic system. This strategy allows for late‑stage diversification of the side chain.

Esterification and Hydrolysis

Formation of an ester from a carboxylic acid and an alcohol, followed by selective hydrolysis of the ester to the corresponding acid, can generate compounds with both ester and acid functionalities. Controlled hydrolysis conditions prevent over‑cleavage of sensitive amide bonds.

Biocatalytic Approaches

Enzymatic synthesis using lipases or amidases offers regio‑selective transformations under mild conditions. For example, a lipase-catalyzed acyl transfer can convert a phenol to a phenolic ester, while maintaining stereochemical integrity at adjacent chiral centers.

Physical and Chemical Properties

Melting and Boiling Points

Melting points of C10H13NO4 compounds vary widely, from below 50 °C for flexible ester‑containing molecules to above 200 °C for rigid amide‑rich structures. Boiling points are typically in the range of 250–350 °C, influenced by the balance between hydrogen‑bonding and lipophilicity.

Solubility Profiles

Solubility in water is often limited (

Stability Under Physical Conditions

Amide bonds confer thermal stability, but the presence of phenolic groups makes the molecule susceptible to oxidation under light or in the presence of metal catalysts. Acidic conditions can trigger hydrolysis of ester linkages, while basic environments promote nucleophilic acyl substitution.

UV‑Visible Absorption

Compounds containing an aromatic core exhibit absorption bands near 260–280 nm, characteristic of π→π* transitions. Additional bands appear around 320–350 nm when conjugated with a β‑ketoester or enol ether motif, offering a simple spectroscopic fingerprint for identification.

pKa and Ionization Behavior

Phenolic hydroxyls typically have pKa values around 9–10, making them weakly acidic in aqueous solution. Carboxylic acids exhibit pKa values near 4–5, leading to deprotonation at physiological pH and enabling salt formation. The amide nitrogen does not ionize under physiological conditions.

Applications

Pharmaceuticals

Many analgesics and anti‑inflammatory agents are N‑methylated phenylacetamides, sharing the C10H13NO4 formula. Their ability to occupy hydrophobic pockets in target enzymes while forming hydrogen bonds with active-site residues underpins their therapeutic efficacy. Example classes include certain selective COX‑2 inhibitors and monoamine reuptake modulators.

Agrochemicals

Herbicides and insecticides featuring a phenolic amide scaffold are common. The lipophilicity imparted by N‑alkyl groups enhances soil adsorption, while ester linkages allow for controlled release of active moieties through hydrolysis in the field.

Material Science

Specialty polymers synthesized from C10H13NO4 monomers incorporate amide cross‑links, improving tensile strength and thermal resistance. Additionally, phenolic resins derived from these molecules exhibit excellent flame‑retardant properties due to the presence of aromatic and carbonyl groups.

Analytical Standards

Reference materials with the formula C10H13NO4 are employed as calibration standards for high‑performance liquid chromatography (HPLC) and gas chromatography (GC) systems. Their defined purity and well-characterized retention times aid in the quantification of complex mixtures.

Analytical Determination

Chromatographic Techniques

Thin‑layer chromatography (TLC) with a solvent system of ethyl acetate/hexane (1:4) typically resolves C10H13NO4 compounds within 5–15 min. HPLC employing a reverse‑phase C18 column and a gradient of water with 0.1 % formic acid to acetonitrile provides high resolution, with retention times reflecting the relative hydrophobicity of the substituents.

Spectroscopic Identification

1H NMR spectra display characteristic multiplets for aromatic protons (δ 7.2–7.5 ppm) and singlets for N‑methyl protons (δ 2.9–3.0 ppm). 13C NMR shows a carbonyl carbon at δ 165–170 ppm and aromatic carbons between δ 120–140 ppm. Infrared (IR) spectra reveal amide N–H stretches near 3300 cm⁻¹ and carbonyl stretches at 1650–1700 cm⁻¹.

Safety and Regulatory Aspects

Health Hazards

Compounds of this formula are generally classified as irritants, with potential for skin and eye irritation. Inhalation exposure to fine particulates may lead to respiratory tract irritation. Some amide‑bearing molecules are metabolized to reactive intermediates that can elicit hepatotoxicity in high doses.

Environmental Impact

Esters and phenolic compounds can undergo biodegradation through hydrolysis and oxidation. The rate of degradation depends on the substitution pattern; electron‑donating methoxy groups often slow metabolic breakdown, leading to prolonged environmental persistence. Regulatory agencies monitor such compounds for bioaccumulation potential.

Regulatory Status

When present in pharmaceutical preparations, C10H13NO4 derivatives are subject to guidelines set forth by the International Council for Harmonisation (ICH) and the Food and Drug Administration (FDA). Specific guidelines cover acceptable daily intake (ADI), maximum residue limits (MRL) for agrochemicals, and permissible levels in consumer products.

Research and Development

Drug Discovery Initiatives

Structure‑activity relationship (SAR) studies frequently target the amide region in C10H13NO4 scaffolds to optimize binding affinity and pharmacokinetic properties. High-throughput screening campaigns have identified several lead compounds featuring this formula, with modifications at the nitrogen and aromatic positions leading to significant potency enhancements.

Metabolic Profiling

In vitro assays using human liver microsomes assess the metabolic stability of these compounds. Key enzymes such as cytochrome P450 2D6 and 3A4 metabolize N‑methyl groups, producing N‑demethylated metabolites that retain the core structure but differ in activity.

Material Science Explorations

Researchers are investigating the use of C10H13NO4 monomers in the synthesis of thermally stable polymers for electronic applications. The combination of aromatic cores and amide cross‑links yields materials with high dielectric constants and low dielectric loss, suitable for capacitor substrates.

Conclusion

Compounds sharing the molecular formula C10H13NO4 embody a rich landscape of structural motifs, functional groups, and physicochemical behaviors. Their prevalence in drug development, agrochemical production, and advanced materials underscores the importance of a comprehensive understanding of their synthesis, analysis, and safety profiles. Continued research into the design and optimization of these molecules promises further advances across multiple scientific domains.

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