P Nitrophenol Ph

Understanding p-Nitrophenol and its pH-Dependent Properties

p-Nitrophenol (PNP) is a chemical compound that exhibits fascinating behavior related to pH. Understanding this behavior is crucial in various fields, from chemistry and biochemistry to environmental science and analytical techniques. This article will demystify the relationship between p-nitrophenol and pH, explaining its properties in a clear and accessible manner.

1. The Structure and Nature of p-Nitrophenol

p-Nitrophenol gets its name from its chemical structure. It's a phenol molecule (a benzene ring with a hydroxyl group, -OH) with a nitro group (-NO₂) attached to the para position (opposite) of the hydroxyl group. This seemingly simple structural difference profoundly influences its properties. The nitro group is an electron-withdrawing group, meaning it pulls electron density away from the rest of the molecule. This affects the acidity of the hydroxyl group.

2. p-Nitrophenol as a Weak Acid

Phenols, including p-nitrophenol, are weak acids. This means they only partially dissociate in water, releasing a proton (H⁺) and forming a negatively charged phenoxide ion. The equilibrium reaction can be represented as follows:

p-NO₂-C₆H₄-OH ⇌ p-NO₂-C₆H₄-O⁻ + H⁺

The equilibrium lies largely to the left, indicating that most of the p-nitrophenol remains in its undissociated form. The position of this equilibrium, and therefore the extent of dissociation, is heavily influenced by the pH of the solution.

3. The Impact of pH on p-Nitrophenol's Color and Absorption

This is where the magic happens. p-Nitrophenol displays a distinct color change depending on the pH of the solution. In acidic solutions (low pH), it exists primarily in its colorless, neutral form. As the pH increases (becoming more alkaline), the equilibrium shifts to the right, favoring the formation of the yellow phenoxide ion. This color change is dramatic and visually striking. This property makes p-nitrophenol a useful indicator in acid-base titrations and other chemical analyses.

The color change is directly linked to the absorption of light. The neutral form absorbs ultraviolet (UV) light, while the yellow phenoxide ion absorbs visible light, specifically in the yellow-green region of the spectrum. Spectrophotometry, a technique measuring light absorbance, utilizes this property to quantify p-nitrophenol concentrations in solutions. For instance, monitoring the absorbance at a specific wavelength (e.g., 400 nm) as pH changes can precisely determine the pKa of p-nitrophenol.

4. pKa and its Significance

The pKa is a crucial value representing the acidity of a compound. It's the pH at which exactly half of the p-nitrophenol molecules are in their dissociated (phenoxide ion) form and half are in their undissociated (neutral) form. The pKa of p-nitrophenol is approximately 7.15. This means that at pH 7.15, the solution will contain equal concentrations of the colorless and yellow forms, resulting in a pale yellow appearance. Below this pH, the solution is predominantly colorless; above this pH, it becomes increasingly yellow.

5. Practical Applications

The pH-dependent color change of p-nitrophenol has several practical applications:

Acid-base titrations: It acts as a visual indicator, signaling the endpoint of a titration.
Enzyme assays: Certain enzymes produce or utilize p-nitrophenol as a substrate or product. The resulting color change can be quantitatively measured to determine enzyme activity. For example, the activity of phosphatases is often monitored using p-nitrophenyl phosphate, which is hydrolyzed to release p-nitrophenol.
Environmental monitoring: PNP's presence can indicate certain environmental pollution events or microbial activity. The colorimetric analysis helps in its detection and quantification.

Actionable Takeaways:

p-Nitrophenol’s color changes dramatically with pH, transitioning from colorless to yellow as the pH increases.
This color change is due to the equilibrium between the neutral and charged forms of the molecule.
The pKa of p-nitrophenol (approximately 7.15) is the pH at which half of the molecules are ionized.
This property has numerous applications in chemistry, biochemistry, and environmental science.

FAQs:

1. What is the difference between p-nitrophenol and o-nitrophenol? The difference lies in the position of the nitro group on the benzene ring. In p-nitrophenol, it's opposite the hydroxyl group (para position), whereas in o-nitrophenol, it's adjacent (ortho position). This affects their acidity and other properties.

2. Is p-nitrophenol toxic? Yes, p-nitrophenol is toxic and should be handled with appropriate safety precautions. Always wear appropriate personal protective equipment (PPE) and work in a well-ventilated area.

3. How can I determine the pKa of p-nitrophenol experimentally? You can do this using spectrophotometry. By measuring the absorbance at a specific wavelength as you change the pH of a p-nitrophenol solution, you can plot the data and determine the pKa from the resulting titration curve.

4. What is the best wavelength to measure the absorbance of p-nitrophenol? The optimal wavelength depends on whether you are measuring the neutral or ionized form. The ionized form has a strong absorbance around 400 nm.

5. Can p-nitrophenol be used as a pH indicator in all types of titrations? While it's useful for many, its pKa of 7.15 limits its effectiveness for titrations far outside this pH range. Other indicators with different pKa values are preferred for strong acid-strong base or very acidic/basic titrations.

Search Results:

Adsorption characteristics and mechanism of p-nitrophenol by … 20 Mar 2020 · Importantly, p-nitrophenol exists mainly in anionic form (C 6 H 4 NO 3 −) at pH values above 7, so that a strong electrostatic repulsion exists between biochar and p …

Modelling the pH dependence of the kinetics of aerobic p-nitrophenol ... 28 Feb 2011 · There are a number of publications in the literature that might indicate a connection between pH and the kinetics of the aerobic p -nitrophenol (PNP) biodegradation.

Revisiting the fundamentals of p-nitrophenol analysis for its ... 31 Jul 2020 · The aim of this paper is to offer a graphical update of how pH and temperature affect the p-nitrophenol absorbance at different wavelengths in lipase emulsified media, due to its …

Effect of the solution’s pH on p-nitrophenol ... - ResearchGate The solution’s pH was adjusted to 3–11 by adding 0.1 mol/L NaOH or 0.1 mol/L HCl, and the pH value was basically kept constant during the adsorption process.

4-Nitrophenol CAS 100-02-7 | 106798 - Merck 4-Nitrophenol CAS 100-02-7 indicator - Find MSDS or SDS, a COA, data sheets and more information.

4-Nitrophenol - Wikipedia 4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of the hydroxyl group on the benzene ring. 4-nitro …

Sonolysis of aqueous 4-nitrophenol at low and high pH 1 Jan 2000 · A detailed product study of the sonolysis of 4-nitrophenol solutions shows that at pH 10, where 4-nitrophenol is deprotonated (p Ka =7.1), its sonolytic degradation is fully …

Ultraviolet absorption spectrum of PNP at various pH values. The ... In this study, the isosbestic point of p-nitrophenol was found and used as the marker for its activity. The methodology avoided decomposition of the substrate, chromophore agents, and …

Ionic Liquid Induced p-Nitrophenol prototropism - ScienceDirect 1 Jun 2023 · Among the various nitrophenols, p-Nitrophenol (PNP) is used as a pH indicator, precursor for the preparation of phenetidine, acetophenetidine and intermediate in the …

4-Nitrophenol | 100-02-7 - ChemicalBook 27 Jan 2025 · Indicator in 0.1% alcohol solution. pH: 5.6 colorless, 7.6 yellow. It can be used to prepare 4-aminophenol (4-AP), a key intermediate for the manufacture of analgesic and …

Efficient Ground-State Recovery of UV-Photoexcited p-Nitrophenol … 25 Oct 2024 · Here, we explore the photochemical fates of a model nitroaromatic chromophore, p-nitrophenol (p-NP), in aqueous solution, and the dependence of its photochemistry on pH.

p-nitrophenol: characteristics, uses and toxicity - science - 2025 13 Aug 2021 · P-nitrophenol is a pH indicator that is colorless at pH below 5.4 and is yellow above 7.5. On the other hand, this compound is used for the synthesis of various substances of …

4-Nitrophenol - an overview | ScienceDirect Topics 4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of hydroxyl group on the benzene ring. You might …

Spectrophotometric Determination of p-Nitrophenol under ENP ... In this paper, a novel technique of spectrophotometric determination of p -nitrophenol (PNP) was developed under the interfering impact of nano-Fe (OH) 3, widely distributed in the natural …

UV-Vis absorption spectra of PNP at different pH values and ... At a pH of 3.7, pure THQ exhibits three peaks at approximately 270 nm, 330 nm, and 360 nm, which originate from the π → π* interactions corresponding to the aromatic ring and the η → π*...

Ozonation of p-nitrophenol at different pH values of water and the ... 1 Mar 2015 · Ozonation of p -nitrophenol was carried out at constant pH values of 2, 7 and 10. Radical scavenger t -butanol was used for different t -butanol concentrations. pH determines …

Determining the pKa of p-Nitrophenol Study Guide - Quizlet 22 Nov 2024 · At acidic pH, p-nitrophenol is colorless, indicating it is in its undissociated form. At alkaline pH, the p-nitrophenolate ion predominates, which is yellow and absorbs light in the …

Nitrophenol - Wikipedia p-Nitrophenol, yellow solid is a precursor to the rice herbicide fluorodifen, the pesticide parathion, and the human analgesic paracetamol (also known as acetaminophen). The mononitrated …

4-Nitrophenol | C6H5NO3 | CID 980 - PubChem 4-nitrophenol is a member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group. It has a role as a human …