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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Valence Bond Theory02:42

Valence Bond Theory

Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
DNA Base Pairing02:27

DNA Base Pairing

Erwin Chargaff’s rules on DNA equivalence paved the way for the discovery of base pairing in DNA. Chargaff’s rules state that in a double-stranded DNA molecule,

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Updated: May 30, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Multiple hydrogen-bonded complexes based on 2-ureido-4[1H]-pyrimidinone: a theoretical study.

Hao Sun1, Hui Hui Lee, Idriss Blakey

  • 1Faculty of Chemistry, Institute of Functional Material Chemistry, Northeast Normal University, 130024 Changchun, Jilin, People's Republic of China.

The Journal of Physical Chemistry. B
|August 13, 2011
PubMed
Summary

This study explores 2-ureido-4[1H]-pyrimidinone (UPy) dimers, finding they prefer specific hydrogen-bonded arrays. Solvent polarity significantly impacts dimerization, with water disrupting UPy dimer formation.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Last Updated: May 30, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Published on: April 10, 2015

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

  • Computational Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • 2-ureido-4[1H]-pyrimidinone (UPy) derivatives are crucial in supramolecular chemistry for their hydrogen bonding capabilities.
  • Understanding the self-assembly behavior of UPy monomers and dimers in different environments is key to designing novel functional materials.
  • Previous studies have focused on UPy hydrogen bonding, but a comprehensive analysis across various solvents using advanced theoretical methods is needed.

Purpose of the Study:

  • To investigate the electronic structures and properties of UPy-based monomers and dimers.
  • To analyze the influence of different environments (vacuum, chloroform, water) on UPy dimer formation and stability.
  • To explore the impact of substituents and solvent polarity on dimerization energetics and hydrogen bond characteristics.

Main Methods:

  • Density Functional Theory (DFT) methods were employed to study UPy monomers and dimers.
  • Topological analysis was used to characterize intramolecular and intermolecular hydrogen bonds.
  • Frequency and Natural Bond Orbital (NBO) calculations were performed to analyze hydrogen bond strength and vibrational properties.

Main Results:

  • UPy dimers predominantly form DDAA-AADD hydrogen-bonded arrays in vacuum and solvents.
  • Hydrogen bonds in UPy dimers exhibit significant red shifts in vibrational frequencies.
  • Electron-donating substituents at position 6 enhance dimerization binding energy; increased solvent polarity, especially water, hinders dimerization.

Conclusions:

  • UPy dimer formation is favored by specific hydrogen bonding arrangements and influenced by substituent effects.
  • Solvent polarity plays a critical role, with polar solvents like water disrupting UPy dimer structures.
  • DFT calculations provide valuable insights into the factors governing UPy self-assembly for potential applications in materials science.