Organic stereochemistry
A curated selection of authoritative references, interactive molecular tools and broader educational resources relevant to organic stereochemistry and molecular symmetry.
The resources listed here are external materials selected for their educational or scientific value. “Free access” does not necessarily mean that material is openly licensed for reuse.
IUPAC Recommendations 2006
Recommendations for unambiguous two-dimensional depiction of the three-dimensional configuration of molecules. Topics include stereobonds, projections, tetrahedral and non-tetrahedral configurations, allenes, hindered biaryls, planar chirality and helicenes.
Link checked: 20 August 2026
IUPAC · Nomenclature of Organic Chemistry
The principal modern reference for specification of configuration and conformation in organic nomenclature. It covers the CIP system and sequence rules, stereogenic units, stereodescriptors, relative configuration and conformational descriptors.
Link checked: 20 August 2026
IUPAC Recommendations 1996
A coherent reference to established stereochemical terminology. Particularly useful for chirality (types of chirality), optical activity, stereoisomerism, stereogenic units, configurations and conformations and historical stereochemical usage.
Link checked: 20 August 2026
IUPAC Compendium of Chemical Terminology · online version 5.0.0
The searchable IUPAC compendium for checking individual chemical definitions and tracing them to their source recommendations. Especially useful when stereochemical terminology is ambiguous, overlaps with older usage or requires an authoritative definition.
Link checked: 20 August 2026
Chemistry LibreTexts · Organic Chemistry with a Biological Emphasis · Tim Soderberg
A freely accessible chapter that provides a coherent introduction to conformational and configurational stereochemistry. It covers open-chain and cyclic conformations, chirality, R/S nomenclature, optical activity, multiple stereogenic centers, meso compounds, projections, alkene stereochemistry and prochirality.
Link checked: 20 August 2026
Chemistry LibreTexts · Basic Principles of Organic Chemistry · John D. Roberts & Marjorie C. Caserio
Practical aspects of stereochemistry, particularly with regard to chiral compounds, covering optical activity, enantiomeric purity, racemization, chiral resolution, absolute and relative configuration and some other concepts.
Link checked: 20 August 2026
ACS Division of Organic Chemistry
An extensive collection of organic chemistry data developed largely from the Hans Reich Collection and now maintained by the ACS Division of Organic Chemistry. The collection covers a very broad range of topics, including structural information, organic reactions, nomenclature, stereochemistry, physical properties and substantial NMR resources.
Link checked: 20 August 2026
Tim Wallace · University of Manchester
A substantial web-based stereochemistry course developed for undergraduate teaching. It covers conformational and configurational stereochemistry, stereogenic centers and axes, stereoisomerism, topicity and prochirality, and the resolution and analysis of enantiomers. Interactive JSmol molecular models and accompanying exercises support the text throughout.
Link checked: 21 August 2026
Blog · Curated by Valliappan Kannappan and contributors
A large, actively updated portal devoted specifically to chirality with focus on medical and pharmaceutical chemistry. Its stereochemistry material ranges from fundamental concepts and nomenclature to stereoselective synthesis, analytical methods, chiral drugs, natural products and other applications. Particularly useful for breadth and for links between stereochemical principles and pharmaceutical or analytical practice.
Link checked: 20 August 2026
Otterbein University
An extensive interactive gallery of more than 120 molecules and polyhedra organized by point group. Symmetry elements can be displayed directly and the corresponding operations animated, making the gallery especially useful for developing a visual understanding of molecular symmetry.
Link checked: 20 August 2026
Jmol / St. Olaf College
A compact browser-based tool for loading or drawing molecular structures, converting them to 3D and displaying Jmol-calculated CIP descriptors. Useful for testing examples and exploring how descriptor assignments respond to structural changes.
Link checked: 20 August 2026