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

Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

34.5K
sp3d and sp3d 2 Hybridization
34.5K
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

50.0K
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
50.0K
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.2K
Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the...
1.2K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

10.2K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
10.2K
Valence Bond Theory and Hybridized Orbitals02:38

Valence Bond Theory and Hybridized Orbitals

23.7K
According to valence bond theory, a covalent bond results when: (1) an orbital on one atom overlaps an orbital on a second atom, and (2) the single electrons in each orbital combine to form an electron pair. The strength of a covalent bond depends on the extent of overlap of the orbitals involved. Maximum overlap is possible when the orbitals overlap on a direct line between the two nuclei.
A σ bond (single bond in a Lewis structure) is a covalent bond in which the electron density is...
23.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.8K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.8K

You might also read

Related Articles

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

Sort by
Same author

Selective Inhibition of KRASG13C Reveals an Increased Dependence on Wild-Type RAS Isoforms in Codon 13 RAS-Mutant Cancers.

Cancer discovery·2026
Same author

Biosynthesis of the Selenium-Substituted [FeFe]-Hydrogenases.

Journal of the American Chemical Society·2026
Same author

Generalized Analysis of Electrophilic Small Molecules.

Angewandte Chemie (International ed. in English)·2026
Same author

Evaluating the Association Between Core Muscle Injury Symptom Pattern and Concomitant Femoroacetabular Impingement Syndrome.

Orthopaedic journal of sports medicine·2026
Same author

Synthesis and Optical Quantum Memory Characterization of α-Eu(IO<sub>3</sub>)<sub>3</sub>, β-Eu(IO<sub>3</sub>)<sub>3</sub>, and NaEu(IO<sub>3</sub>)<sub>4</sub>.

Inorganic chemistry·2026
Same author

Cancer Susceptibility to Stapled Oncolytic Peptides Is Dictated by Membrane Cholesterol and Inflammatory Signaling.

Cancer research·2026
Same journal

Daily briefing: 'Cyborg' cockroaches breathe underwater with printed suit.

Nature·2026
Same journal

China boosts prestigious grants for young scientists - will it ease competition?

Nature·2026
Same journal

Incoming US science academy chief vows to 'double down' on research.

Nature·2026
Same journal

Author Correction: Synthesis of enantioenriched atropisomers by biocatalytic deracemization.

Nature·2026
Same journal

Electrodeposited self-assembled molecules for perovskite photovoltaics.

Nature·2026
Same journal

Neutrino's nursery found: the 'Shadow Blaster'.

Nature·2026
See all related articles

Related Experiment Video

Updated: Oct 4, 2025

Rapid in-silico Battery Electrolyte Electrochemical Reaction Generation using 3T-VASP Multi-Scale Energy Minimization
05:37

Rapid in-silico Battery Electrolyte Electrochemical Reaction Generation using 3T-VASP Multi-Scale Energy Minimization

Published on: August 22, 2025

153

Automated iterative Csp3-C bond formation.

Daniel J Blair1, Sriyankari Chitti2, Melanie Trobe2

  • 1Roger Adams Laboratory, School of Chemical Sciences, University of Illinois at Urbana-Champaign, Urbana, IL, USA. danielb@illinois.edu.

Nature
|February 8, 2022
PubMed
Summary
This summary is machine-generated.

New tetramethyl N-methyliminodiacetic acid (TIDA) boronates enable automated synthesis of complex molecules by facilitating stereospecific Csp³-C bond formation, expanding access to functional organic compounds.

More Related Videos

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

10.6K
Interactive Molecular Model Assembly with 3D Printing
06:15

Interactive Molecular Model Assembly with 3D Printing

Published on: August 13, 2020

10.3K

Related Experiment Videos

Last Updated: Oct 4, 2025

Rapid in-silico Battery Electrolyte Electrochemical Reaction Generation using 3T-VASP Multi-Scale Energy Minimization
05:37

Rapid in-silico Battery Electrolyte Electrochemical Reaction Generation using 3T-VASP Multi-Scale Energy Minimization

Published on: August 22, 2025

153
Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

10.6K
Interactive Molecular Model Assembly with 3D Printing
06:15

Interactive Molecular Model Assembly with 3D Printing

Published on: August 13, 2020

10.3K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Chemical Engineering

Background:

  • Automated synthesis offers on-demand access to small molecules, but current methods are limited.
  • Automating stereospecific Csp³-C bond formation is crucial for accessing diverse functional organic molecules.
  • Previous methyliminodiacetic acid (MIDA) boronates are unsuitable for stereospecific Csp³-C bond-forming reactions.

Purpose of the Study:

  • To develop a new class of boronates compatible with automated stereospecific Csp³-C bond formation.
  • To overcome the limitations of existing MIDA boronates in complex molecule synthesis.

Main Methods:

  • Development of tetramethyl N-methyliminodiacetic acid (TIDA) boronates through hyperconjugative and steric tuning.
  • Charge density analysis to understand N-B bond stability and hydrolysis.
  • Steric shielding of carbonyl π-faces to control reactivity.

Main Results:

  • TIDA boronates exhibit enhanced stability against hydrolysis and reduced reactivity towards nucleophiles.
  • The iminodiacetic acid cage features essential for automated synthesis are preserved in TIDA boronates.
  • Automated synthesis of Csp³ boronate building blocks and natural products via stereospecific Csp³-Csp² and Csp³-Csp³ bond formation was achieved.

Conclusions:

  • TIDA boronates represent a significant advancement in automated synthetic chemistry.
  • This new class of boronates enables the synthesis of complex Csp³-rich small molecules.
  • The findings pave the way for broader applications of automated synthesis in organic chemistry.