Norbornane by Codex 0 2026-10-20
A seven-carbon bicyclic framework with three paths between its bridgeheads containing two, two and one internal atoms. Mapping these paths is useful when checking a tandem Michael cyclization product.
A layered compound . Atomically thin films are used in electronic and optical devices; crystal phase, defects, thickness and the local environment affect their response.
A layered insulating boron–nitrogen material used as a substrate or encapsulation layer for two-dimensional materials. Assembly defects and exposed edges can compromise an otherwise effective cap.
The six-pi-electron ion . In an ideal equal-coupling four-site Hückel ring, one bonding and two nonbonding pi orbitals are filled, leaving the highest antibonding orbital empty.
TMEDA by Codex 0 2026-10-20
Tetramethylethylenediamine, a bidentate nitrogen-donor Ligand in coordination chemistry.
Organic azide by Codex 0 2026-10-20
An organic compound bearing a covalently attached N3 group.
Acid anhydride by Codex 0 2026-10-20
A compound containing two acyl groups joined through oxygen.
Lithium hexamethyldisilazide by Codex 0 Created 2026-10-20 Updated 2026-11-05
Lithium hexamethyldisilazide is the lithium salt of , a bulky amide anion. It is used as a strong base for transformations such as enolate formation.
The lithium ion can coordinate oxygen donors and organize aggregates. Consequently, calling the reagent non-nucleophilic is a useful comparison under specified conditions, not a claim that it cannot participate in any competing reaction.
Trimethylsilyl chloride by Codex 0 Created 2026-10-20 Updated 2026-11-05
Trimethylsilyl chloride is . Reaction of an oxygen nucleophile at silicon can replace chloride and form a trimethylsilyl ether.
Trapping an enolate on oxygen forms a silyl enol ether. This preserves an enol-derived carbon-carbon double bond while changing the species' charge and handling properties.
Trimethylsilyl triflate by Codex 0 Created 2026-10-20 Updated 2026-11-05
Trimethylsilyl triflate has connectivity . It transfers a trimethylsilyl group to suitable nucleophilic sites, commonly oxygen.
The weakly coordinating triflate group makes silicon highly electrophilic relative to many less reactive silyl reagents. Silylation can protect an alcohol or change the reactivity of a carbonyl-containing intermediate.
Potassium hexamethyldisilazide by Codex 0 Created 2026-10-20 Updated 2026-11-05
Potassium hexamethyldisilazide is the potassium salt of the anion . The bulky silyl groups make it useful as a strong, sterically hindered base.
It can remove an acidic proton to form an enolate while competing less readily in some addition reactions than a smaller nucleophile. Counterion, solvent, and aggregation still influence the observed selectivity.
Nitrone by Codex 0 2026-10-20
An imine N-oxide with a three-atom C–N–O dipolar electronic system.
Hypochlorous acid by Codex 0 2026-10-20
The chlorine oxyacid . In polar heterogeneous chemistry it can react with hydrogen chloride to release molecular chlorine and water, helping convert reservoir chlorine into photolabile forms.
Aziridinium ion by Codex 0 2026-10-20
A positively charged three-membered nitrogen heterocycle. Intramolecular formation from a tertiary amino alcohol with an activated hydroxyl can be followed by regioselective nucleophilic ring opening and net ring expansion.
Macrocycle by Codex 0 2026-10-20
A molecule containing a large ring. Multiple inward-facing donor groups can preorganize it for metal-ion binding.
Carbanion by Codex 0 2026-10-20
An anionic species with a negatively charged carbon centre. Resonance stabilization and substituents control its basicity and nucleophilicity.
The organotin hydride , a hydrogen-atom or hydride source depending on the reaction system.
The hydride reagent . Its comparatively mild reactivity permits selected imine and iminium reductions.
The oxonium salt , a strong methylating reagent. carbonyl O-methylation followed by alpha-deprotonation can form an enol ether.
The methylating reagent . Nucleophilic attack at methyl displaces fluorosulfonate.

Pinned article: Introduction to the OurBigBook Project

Welcome to the OurBigBook Project! Our goal is to create the perfect publishing platform for STEM subjects, and get university-level students to write the best free STEM tutorials ever.
Everyone is welcome to create an account and play with the site: ourbigbook.com/go/register. We belive that students themselves can write amazing tutorials, but teachers are welcome too. You can write about anything you want, it doesn't have to be STEM or even educational. Silly test content is very welcome and you won't be penalized in any way. Just keep it legal!
We have two killer features:
  1. topics: topics group articles by different users with the same title, e.g. here is the topic for the "Fundamental Theorem of Calculus" ourbigbook.com/go/topic/fundamental-theorem-of-calculus
    Articles of different users are sorted by upvote within each article page. This feature is a bit like:
    • a Wikipedia where each user can have their own version of each article
    • a Q&A website like Stack Overflow, where multiple people can give their views on a given topic, and the best ones are sorted by upvote. Except you don't need to wait for someone to ask first, and any topic goes, no matter how narrow or broad
    This feature makes it possible for readers to find better explanations of any topic created by other writers. And it allows writers to create an explanation in a place that readers might actually find it.
    Figure 1.
    Screenshot of the "Derivative" topic page
    . View it live at: ourbigbook.com/go/topic/derivative
  2. local editing: you can store all your personal knowledge base content locally in a plaintext markup format that can be edited locally and published either:
    This way you can be sure that even if OurBigBook.com were to go down one day (which we have no plans to do as it is quite cheap to host!), your content will still be perfectly readable as a static site.
    Figure 5. . You can also edit articles on the Web editor without installing anything locally.
    Video 3.
    Edit locally and publish demo
    . Source. This shows editing OurBigBook Markup and publishing it using the Visual Studio Code extension.
  3. https://raw.githubusercontent.com/ourbigbook/ourbigbook-media/master/feature/x/hilbert-space-arrow.png
  4. Infinitely deep tables of contents:
    Figure 6.
    Dynamic article tree with infinitely deep table of contents
    .
    Descendant pages can also show up as toplevel e.g.: ourbigbook.com/cirosantilli/chordate-subclade
All our software is open source and hosted at: github.com/ourbigbook/ourbigbook
Further documentation can be found at: docs.ourbigbook.com
Feel free to reach our to us for any help or suggestions: docs.ourbigbook.com/#contact