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Related Concept Videos

Keto–Enol Tautomerism: Mechanism01:14

Keto–Enol Tautomerism: Mechanism

The keto and enol forms are known as tautomers and they constantly interconvert (or tautomerize) between the two forms under acid or base catalyzed conditions. Both the reactions involve the same steps—protonation and deprotonation— although in the reverse order.
Stereoisomerism02:52

Stereoisomerism

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...
Isomerism02:43

Isomerism

Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
Stereoisomers02:32

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to restricted...
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
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...

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Related Experiment Video

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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

Let's not forget tautomers.

Yvonne Connolly Martin1

  • 1Martin Consulting, 2230 Chestnut St., Waukegan, IL 60087, USA. yvonnecmartin@comcast.net

Journal of Computer-Aided Molecular Design
|October 21, 2009
PubMed
Summary
This summary is machine-generated.

Tautomerism, the ability of a compound to exist in multiple forms, challenges computer-aided molecular design. Accurately modeling tautomers is crucial for drug discovery and property prediction.

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Area of Science:

  • Chemical structure and dynamics
  • Computational chemistry
  • Drug discovery

Background:

  • Tautomerism involves intramolecular hydrogen movement, creating distinct molecular forms.
  • Tautomers exhibit varied properties (fingerprints, hydrophobicity, pKa, 3D shape, electrostatics).
  • Proteins may preferentially bind low-abundance tautomers, complicating molecular recognition.

Purpose of the Study:

  • To highlight the challenges posed by tautomerism in computer-aided molecular design.
  • To underscore the impact of tautomerism on library design, property prediction, and QSAR.
  • To identify the need for better methods to handle tautomerization in computational chemistry.

Main Methods:

  • The study is a review and analysis of existing challenges and methodologies.
  • It discusses the implications of tautomerism on various computational chemistry techniques.
  • It highlights the lack of comprehensive databases and consensus on computational methods.

Main Results:

  • Approximately 25% of chemical databases contain tautomerizable molecules.
  • Inaccurate handling of tautomers affects molecular similarity, diversity, and property prediction.
  • Decisions regarding tautomer inclusion and scoring are difficult in QSAR and docking.

Conclusions:

  • Properly accounting for tautomerism is essential for accurate computer-aided molecular design.
  • There is a critical need for better experimental data and computational methods for tautomeric ratios.
  • Addressing tautomerism is vital for improving the reliability of drug discovery and development processes.