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Stereoisomerism02:52

Stereoisomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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Stereoisomerism of Cyclic Compounds02:33

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Factors Affecting Dissolution: Polymorphism, Amorphism and Pseudopolymorphism01:21

Factors Affecting Dissolution: Polymorphism, Amorphism and Pseudopolymorphism

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Polymorphism refers to the existence of a drug substance in multiple crystalline forms, known as polymorphs. Recently, this term has been expanded to include solvates (forms containing a solvent), amorphous forms (non-crystalline forms), and desolvated solvates (forms from which the solvent has been removed).
Some polymorphic crystals possess lower aqueous solubility than their amorphous counterparts, leading to incomplete absorption. For instance, the oral suspension of Chloramphenicol, which...
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
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Naming Enantiomers02:21

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
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A triclinic polymorph of miconazole.

Hanna Kaspiaruk1,2, Lilianna Chęcińska2

  • 1University of Lodz Doctoral School of Exact and Natural Sciences, Narutowicza 68, 90-136 Łódź, Poland.

Acta Crystallographica. Section E, Crystallographic Communications
|February 9, 2024
PubMed
Summary

This study reports a new triclinic crystal structure for the antifungal drug miconazole (MIC). The new form exhibits different molecular orientations and weaker intermolecular interactions compared to the previously known monoclinic polymorph.

Keywords:
Hirshfeld surfacecrystal structureenergy frameworksmiconazole

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Area of Science:

  • Crystallography
  • Materials Science
  • Pharmaceutical Chemistry

Background:

  • Miconazole (MIC) is a widely used antifungal medication.
  • Polymorphism, the ability of a solid material to exist in multiple crystalline forms, can affect drug properties.
  • Understanding different polymorphs of miconazole is crucial for its formulation and efficacy.

Purpose of the Study:

  • To determine and characterize the crystal structure of a novel triclinic polymorph of miconazole.
  • To compare the structural features and intermolecular interactions of the triclinic polymorph with the previously reported monoclinic polymorph of miconazole.
  • To investigate the role of weak interactions in stabilizing the crystal structures.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the crystal structure of the triclinic miconazole polymorph.
  • Comparative crystallographic analysis was performed between the triclinic and monoclinic forms.
  • Hirshfeld surface analysis and energy framework calculations were utilized to study intermolecular interactions.

Main Results:

  • The crystal structure of the new triclinic polymorph of miconazole (C18H14Cl4N2O) was successfully determined.
  • A distinct orientation of the imidazole ring and one di-chloro-phenyl group was observed in the triclinic form compared to the monoclinic form.
  • Weak interactions, including halogen bonds and C-H⋯π(arene) interactions, were identified as the primary stabilizing forces in the triclinic crystal structure.

Conclusions:

  • The discovery of a new triclinic polymorph expands the understanding of miconazole's solid-state behavior.
  • Differences in molecular packing and intermolecular interactions between polymorphs may influence physicochemical properties.
  • Hirshfeld surface analysis and energy framework calculations provide valuable insights into crystal packing and interactions for drug design.