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Related Concept Videos

Lewis Acids and Bases02:16

Lewis Acids and Bases

16.2K
This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
16.2K
Lewis Acids and Bases02:33

Lewis Acids and Bases

47.7K
In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
47.7K
Polyprotic Acids03:38

Polyprotic Acids

31.5K
Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
31.5K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.2K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.2K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.7K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
10.7K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.6K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.6K

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Updated: Dec 22, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Boric Acid, a Lewis Acid With Unique and Unusual Properties: Formulation Implications.

Antonio Lopalco1, Angela A Lopedota1, Valentino Laquintana1

  • 1Department of Pharmacy - Drug Sciences, Università Degli Studi di Bari Aldo Moro, Bari 70125, Italy.

Journal of Pharmaceutical Sciences
|May 1, 2020
PubMed
Summary

Boric acid serves diverse pharmaceutical roles, acting as an excipient and buffer. While generally safe at low doses, high exposure can lead to toxicity, particularly in children.

Keywords:
Absorption, distribution, metabolism, and excretion (ADME)Boric acidExcipient(s)FormulationPharmacokineticsPhysicochemical propertiesPreformulationToxicology

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Area of Science:

  • Pharmaceutical Science
  • Chemistry

Background:

  • Boric acid is a Lewis acid with a pKa of 8.92-9.24, influenced by concentration, temperature, and ionic strength.
  • It exhibits reversible reactions with alcohols, carboxylic acids, thiols, and amines, forming adducts with lower pKa values.
  • Boric acid's properties allow it to stabilize some substances while catalyzing the degradation of others.

Purpose of the Study:

  • To review the multifaceted applications of boric acid in pharmaceutical formulations.
  • To elucidate its chemical properties and reactivity relevant to drug delivery.
  • To assess its safety profile across various administration routes and dosages.

Main Methods:

  • Literature review of boric acid's chemical properties.
  • Analysis of its use as an excipient, buffer, and active ingredient in pharmaceutical products.
  • Evaluation of toxicological data from human and animal studies.

Main Results:

  • Boric acid functions as a buffer, antibacterial, and antifungal agent in topical and ophthalmic preparations.
  • It is used as an excipient in pharmaceutical formulations, with reactivity dependent on pH and concentration.
  • While safe at low doses, high systemic exposure carries risks, including toxicity in children and reproductive effects in animals.

Conclusions:

  • Boric acid is a versatile pharmaceutical ingredient with established uses in various formulations.
  • Its chemical reactivity and buffering capacity are key to its functionality.
  • Careful consideration of dosage and exposure is crucial due to potential toxicity.