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Related Concept Videos

Experimental Determination of Chemical Formula02:37

Experimental Determination of Chemical Formula

The elemental makeup of a compound defines its chemical identity, and chemical formulas are the most concise way of representing this elemental makeup. When a compound’s formula is unknown, measuring the mass of its constituent elements is often the first step in determining the formula experimentally.
Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered ethane, the...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Determination of Molar Masses of Polymers II01:27

Determination of Molar Masses of Polymers II

Polymer samples typically consist of macromolecular chains with a distribution of lengths, resulting in a range of molar masses rather than a single discrete value. Conventional descriptors such as the number-average molar mass and weight-average molar mass quantify this distribution but do not fully capture polymer behavior in solution..The viscosity-average molar mass provides a more realistic description of polymer behavior in solution because it accounts for the enhanced contribution of...

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Synthesis and Structure Determination of &#181;-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
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Iterative high-throughput polymorphism studies on acetaminophen and an experimentally derived structure for form III.

Matthew L Peterson1, Sherry L Morissette, Chris McNulty

  • 1TransForm Pharmaceuticals, Inc., 610 Lincoln Street, Waltham, Massachusetts 02451, USA.

Journal of the American Chemical Society
|September 13, 2002
PubMed
Summary

A new high-throughput crystallization platform, CrystalMax, enabled the preparation and characterization of three acetaminophen crystal forms. Structural models for the difficult-to-obtain third form were proposed, explaining its challenging preparation.

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Area of Science:

  • Crystallization science
  • Materials science
  • Pharmaceutical science

Background:

  • Acetaminophen exhibits polymorphism, with three known crystal forms.
  • Characterizing and preparing specific polymorphs can be challenging.
  • High-throughput methods offer potential for efficient polymorph screening.

Purpose of the Study:

  • To develop and utilize a high-throughput crystallization platform for acetaminophen polymorph preparation.
  • To characterize the three known crystal forms of acetaminophen.
  • To elucidate the structure of the elusive third acetaminophen crystal form.

Main Methods:

  • Development of a high-throughput crystallization platform (CrystalMax) integrating design software, robotic handling, and microanalytics.
  • Parallel crystallization experiments using diverse supersaturation driving methods.
  • Powder X-ray diffraction (PXRD) analysis for structural elucidation.
  • Computational modeling for structural hypothesis generation.

Main Results:

  • Successful preparation and characterization of three acetaminophen crystal forms using CrystalMax.
  • PXRD data provided insights into the structure of the third acetaminophen polymorph.
  • A proposed bilayer structural model for the third form, stabilized by O-H...O(H) hydrogen bonds.
  • The proposed structure helps explain the difficulties in obtaining this form from solution.

Conclusions:

  • The CrystalMax platform is effective for high-throughput polymorph screening and preparation.
  • The study provides structural insights into the challenging third form of acetaminophen.
  • Understanding crystal structures and preparation methods is crucial for pharmaceutical development.