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Related Concept Videos

Keto–Enol Tautomerism: Mechanism01:14

Keto–Enol Tautomerism: Mechanism

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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.
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Classification of Titrimetric Analysis Based on Reaction Types01:01

Classification of Titrimetric Analysis Based on Reaction Types

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Titrimetric analysis in solution chemistry involves measuring the volume of solutions and is often called volumetric analysis. The standard solution of known concentration in the burette is called the titrant, whereas the solution of unknown concentration in the flask is called the analyte, or titrand. Titrimetric analyses can be classified into four types based on the reactions between the titrant and analyte.
Titrations between an acid and a base lead to neutralization reactions that form...
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Reactivity of Enols01:18

Reactivity of Enols

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Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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Mass Spectrometry: Aromatic Compound Fragmentation01:23

Mass Spectrometry: Aromatic Compound Fragmentation

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Upon ionization, aromatic compounds generate a molecular ion that is observed as a prominent peak in their mass spectra. For example, the molecular ion peak for benzene appears at a mass-to-charge ratio of 78, while toluene is observed at a mass-to-charge ratio of 92. The molecular ion benzene is highly stable and does not readily undergo further fragmentation due to the significant amount of energy required to disrupt the aromatic stability of the benzene ring. In contrast, the molecular ion...
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Tandem Mass Spectrometry01:21

Tandem Mass Spectrometry

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Tandem mass spectrometry is a technique that uses multiple mass analyzers in series to obtain a higher selectivity and reduce chemical noise during analyte detection. Instruments with multiple analyzers separated by an interaction cell enable secondary fragmentation and selected study of the fragment ions.Secondary fragmentations occur in the interaction cell and can be induced by various factors. Fragmentation induced by collision with inert gases, such as N2, Ar, He, etc., is called...
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Chemical Shift: Internal References and Solvent Effects01:17

Chemical Shift: Internal References and Solvent Effects

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In an NMR sample, precise measurement of the absolute absorption frequencies of nuclei is difficult. A standard internal reference compound is added, and the frequency difference between the reference signal and sample signals is measured.
The internal reference compound generally used in NMR spectroscopy is tetramethylsilane (TMS). TMS is preferred because it is chemically inert, soluble in NMR solvents, and easily removable. Also, the highly shielded methyl protons in TMS yield an intense...
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Related Experiment Video

Updated: Dec 29, 2025

PCR Mutagenesis, Cloning, Expression, Fast Protein Purification Protocols and Crystallization of the Wild Type and Mutant Forms of Tryptophan Synthase
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Tautomer Database: A Comprehensive Resource for Tautomerism Analyses.

Devendra K Dhaked1, Laura Guasch1, Marc C Nicklaus1

  • 1Computer-Aided Drug Design Group, Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, NIH, Frederick, Maryland 21702, United States.

Journal of Chemical Information and Modeling
|February 7, 2020
PubMed
Summary
This summary is machine-generated.

A new database catalogs 2,819 tautomeric structures from 171 publications, detailing experimental conditions and chemical identifiers. This resource aids researchers studying tautomerism, particularly prototropic, ring-chain, and valence types.

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Area of Science:

  • Chemical Information Science
  • Computational Chemistry
  • Structural Chemistry

Background:

  • Tautomerism is a fundamental chemical phenomenon involving structural isomers.
  • Databases of chemical structures are crucial for cheminformatics and drug discovery.
  • Comprehensive data on tautomeric forms under various experimental conditions is limited.

Purpose of the Study:

  • To create a comprehensive database of tautomeric structures and their associated experimental conditions.
  • To provide a valuable resource for researchers studying chemical isomerism and reaction mechanisms.
  • To facilitate the development of predictive models for tautomeric behavior.

Main Methods:

  • Extraction of 2,819 tautomeric tuples from 171 scientific publications.
  • Annotation of each entry with experimental conditions, bibliographic details, and structural identifiers (e.g., Standard InChI, SMILES).
  • Categorization of tautomerism types (prototropic, ring-chain, valence) and identification of 77 tautomeric transform rules (SMIRKS).

Main Results:

  • The database contains 5,977 unique structures, primarily tautomeric pairs, with some triples, quadruples, and quintuples.
  • Prototropic tautomerism constitutes the majority (79%), followed by ring-chain (13%) and valence (8%).
  • Data includes information on approximately 50 solvents, 9 solvent mixtures, and 26 spectroscopic/nonspectroscopic methods, with NMR being most frequent.

Conclusions:

  • The developed database offers a rich, experimentally-grounded resource for the study of chemical tautomerism.
  • It provides insights into the prevalence of different tautomerism types and the experimental conditions under which they occur.
  • The database is freely accessible, promoting further research and applications in chemistry and related fields.