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Related Concept Videos

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...
Chirality02:25

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

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Related Experiment Video

Updated: May 15, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Achiral endohedral functionality provides stereochemical control in Fe(II)-based self-assemblies.

Michael C Young1, Amber M Johnson, Ana S Gamboa

  • 1Department of Chemistry, University of California - Riverside, Riverside, California 92521, USA.

Chemical Communications (Cambridge, England)
|January 23, 2013
PubMed
Summary
This summary is machine-generated.

Fe(II)-iminopyridine self-assemblies with varied internal functionality were synthesized. Larger internal groups increase strain, enabling diastereocontrol during assembly, especially with large achiral groups.

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Area of Science:

  • Coordination chemistry
  • Supramolecular chemistry

Background:

  • Fe(II)-iminopyridine complexes are versatile building blocks for self-assembly.
  • Controlling stereochemistry in self-assembled systems remains a challenge.

Purpose of the Study:

  • To synthesize multicomponent Fe(II)-iminopyridine self-assemblies.
  • To investigate the effect of internal functionality size on the assembly process and stereochemical outcome.

Main Methods:

  • Synthesis of Fe(II)-iminopyridine complexes with varying internal cavity sizes.
  • Characterization of self-assembled structures using spectroscopic and crystallographic techniques.

Main Results:

  • Self-assemblies with internal functionalities of different sizes were successfully synthesized.
  • Increased strain from larger internal groups was observed to influence the assembly process.
  • Diastereocontrol was achieved, with complete control observed upon introduction of large achiral groups.

Conclusions:

  • The size of internal functionality in Fe(II)-iminopyridine self-assemblies is a critical factor in controlling diastereoselectivity.
  • Strategic placement of large achiral groups can lead to complete diastereocontrol in these systems.