Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Naming Enantiomers02:21

Naming Enantiomers

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 essentially comprises three steps:...
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...
Prochirality02:05

Prochirality

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...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
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.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

A distributed analysis approach for pharmacovigilance data from electronic medical records in German university hospitals: the POLAR_MI ETL Pipeline.

BMC medical informatics and decision making·2026
Same author

Use of Potentially Inappropriate Medication and Association with Falls During Hospitalisation: An Analysis Based on Electronic Health Records (POLAR_MI project).

Drugs - real world outcomes·2025
Same author

Challenges in detecting and predicting adverse drug events via distributed analysis of electronic health record data from German university hospitals.

PLOS digital health·2025
Same author

Reliability of Multicentric Extracted EMR Data: Quantifying Amitriptyline Use in Elderly Patients - A POLAR_MI Study.

Studies in health technology and informatics·2025
Same author

Prediction of the water solubility by a graph convolutional-based neural network on a highly curated dataset.

Journal of cheminformatics·2025
Same author

The role of cell-cell and cell-matrix junctional complexes in sebaceous gland homeostasis and differentiation.

Cell communication and signaling : CCS·2024

Related Experiment Video

Updated: Jun 10, 2026

A Protocol for Computer-Based Protein Structure and Function Prediction
16:41

A Protocol for Computer-Based Protein Structure and Function Prediction

Published on: November 3, 2011

Tautomer identification and tautomer structure generation based on the InChI code.

Torsten Thalheim1, Armin Vollmer, Ralf-Uwe Ebert

  • 1UFZ Department of Ecological Chemistry, Helmholtz Centre for Environmental Research, Permoserstrasse 15, 04318 Leipzig, Germany.

Journal of Chemical Information and Modeling
|July 30, 2010
PubMed
Summary

A new algorithm rapidly generates all possible prototropic tautomers for organic compounds, revealing that 11% exist in multiple forms. Tautomer variations significantly impact soil sorption and water solubility predictions.

More Related Videos

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

Application of I TASSER, trRosetta, UCSF Chimera, HADDOCK server, and HEX loria for De Novo and In Silico Design of Proteins
05:08

Application of I TASSER, trRosetta, UCSF Chimera, HADDOCK server, and HEX loria for De Novo and In Silico Design of Proteins

Published on: July 8, 2025

Related Experiment Videos

Last Updated: Jun 10, 2026

A Protocol for Computer-Based Protein Structure and Function Prediction
16:41

A Protocol for Computer-Based Protein Structure and Function Prediction

Published on: November 3, 2011

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

Application of I TASSER, trRosetta, UCSF Chimera, HADDOCK server, and HEX loria for De Novo and In Silico Design of Proteins
05:08

Application of I TASSER, trRosetta, UCSF Chimera, HADDOCK server, and HEX loria for De Novo and In Silico Design of Proteins

Published on: July 8, 2025

Area of Science:

  • Computational Chemistry
  • Chemical Informatics
  • Organic Chemistry

Background:

  • Prototropic tautomerism is a fundamental chemical phenomenon involving the migration of protons.
  • Understanding tautomeric diversity is crucial for accurate chemical property prediction and substance registration.
  • Existing methods for enumerating tautomers can be computationally intensive and may not cover all possible forms.

Purpose of the Study:

  • To develop and present a novel algorithm for the rapid and comprehensive generation of prototropic tautomers.
  • To extend the scope of tautomer generation beyond standard InChI (International Chemical Identifier) definitions.
  • To assess the prevalence and impact of tautomerism on chemical properties for a large set of organic compounds.

Main Methods:

  • Development of an algorithm based on InChI code to identify mobile H atoms and heteroatoms.
  • Inclusion of (1,3)-shifts for open chains and (1,n)-shifts (odd n > 3) for ring systems.
  • Extension to include larger (1,n)-shifts by combining conjugated InChI sequences.
  • Application to ~72,500 compounds from the European Inventory of Existing Commercial Chemical Substances (EINECS).
  • Quantitative Structure-Activity Relationship (QSAR) modeling for soil sorption coefficient and water solubility.

Main Results:

  • The algorithm efficiently generates all possible prototropic tautomers.
  • Approximately 11% of tested EINECS compounds exhibit different heteroatom-prototropic tautomeric forms.
  • Tautomerism can lead to variations exceeding two orders of magnitude in soil sorption and four orders of magnitude in water solubility.
  • Quantum chemical analysis suggests thermodynamically stable tautomers often involve H atom exchanges between heteroatoms.

Conclusions:

  • The developed algorithm provides a robust tool for exploring chemical space related to tautomerism.
  • Tautomeric diversity is a significant factor influencing the physicochemical properties of organic substances.
  • Accurate prediction of chemical behavior requires consideration of all relevant tautomeric forms.