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Related Concept Videos

Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
Entropy and Solvation02:05

Entropy and Solvation

The process of surrounding a solute with solvent is called solvation. It involves evenly distributing the solute within the solvent. The rule of thumb for determining a solvent for a given compound is that like dissolves like. A good solvent has molecular characteristics similar to those of the compound to be dissolved. For example, polar solutions dissolve polar solutes, and apolar solvents dissolve apolar solutes. A polar solvent is a solvent that has a high dielectric constant (ϵ ≥ 15); an...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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Updated: May 20, 2026

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
08:12

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Published on: September 5, 2018

Water encapsulation in a polyoxapolyaza macrobicyclic compound.

Pedro Mateus1, Rita Delgado, Patrick Groves

  • 1Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal.

The Journal of Organic Chemistry
|July 28, 2012
PubMed
Summary

A novel heteroditopic macrobicyclic compound was synthesized. Encapsulated water and its unusual protonation behavior were investigated, revealing a surprisingly low fourth protonation constant due to strong water binding.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Physical Chemistry

Background:

  • Development of novel macrocyclic compounds with unique binding properties.
  • Understanding host-guest interactions within complex molecular architectures.
  • Investigating the influence of encapsulated guests on acid-base properties.

Purpose of the Study:

  • Synthesize a new heteroditopic macrobicyclic compound.
  • Characterize its structure and solid-state conformation.
  • Elucidate its acid-base behavior and protonation anomalies in solution.

Main Methods:

  • [1 + 1] "tripod-tripod coupling" synthesis strategy.
  • X-ray crystallography for structural determination.
  • Potentiometry, 1H NMR, and DOSY experiments for solution studies.
  • Molecular modeling for conformational analysis.

Main Results:

  • Successful synthesis of the t(2)pN(5)O(3) macrobicycle in good yield.
  • X-ray structure confirmed encapsulated water molecule stabilized by hydrogen bonds.
  • Potentiometry revealed an unexpectedly low fourth protonation constant (log K(4)(H)).
  • Solution studies (NMR, DOSY, modeling) indicated retention of water encapsulation and conformation.

Conclusions:

  • The synthesized macrobicyclic compound exhibits unique structural and acid-base properties.
  • Strong binding of the encapsulated water molecule, including trifurcated hydrogen bonding, explains the low fourth protonation constant.
  • The study highlights the interplay between molecular structure, guest encapsulation, and acid-base behavior in complex macrocycles.