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  2. Nucleophile - Wikipedia

    en.wikipedia.org/wiki/Nucleophile

    In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. Nucleophilic describes the affinity of a nucleophile to bond with positively charged ...

  3. Nucleophilic substitution - Wikipedia

    en.wikipedia.org/wiki/Nucleophilic_substitution

    In chemistry, a nucleophilic substitution (S N) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate.

  4. Sodium methanethiolate - Wikipedia

    en.wikipedia.org/wiki/Sodium_methanethiolate

    Sodium methanethiolate or sodium thiomethoxide (CH 3 SNa, MeSNa) is the sodium conjugate base of methanethiol.This compound is commercially available as a white solid. It is a powerful nucleophile that can be used to prepare methylthioether and other organic compounds like ethyl bromide.

  5. 1,5-Diazabicyclo (4.3.0)non-5-ene - Wikipedia

    en.wikipedia.org/wiki/1,5-Diazabicyclo(4.3.0)non...

    1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is a chemical compound with the formula C 7 H 12 N 2. [1] It is an amidine base used in organic synthesis. A related compound with related functions is 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The relatively complex nature of the formal names for DBU and DBN (hence the common use of acronyms) reflects the ...

  6. Lewis acids and bases - Wikipedia

    en.wikipedia.org/wiki/Lewis_acids_and_bases

    In the context of a specific chemical reaction between NH 3 and Me 3 B, a lone pair from NH 3 will form a dative bond with the empty orbital of Me 3 B to form an adduct NH 3 •BMe 3. The terminology refers to the contributions of Gilbert N. Lewis. [2] The terms nucleophile and electrophile are sometimes interchangeable with Lewis base and ...

  7. Catalytic triad - Wikipedia

    en.wikipedia.org/wiki/Catalytic_triad

    The nucleophile is most commonly a serine or cysteine, but occasionally threonine or even selenocysteine. The 3D structure of the enzyme brings together the triad residues in a precise orientation, even though they may be far apart in the sequence ( primary structure ).

  8. Alpha effect - Wikipedia

    en.wikipedia.org/wiki/Alpha_effect

    In 1962, Edwards and Pearson (the latter of HSAB theory) introduced the phrase alpha effect for this anomaly. He offered the suggestion that the effect was caused by a transition state (TS) stabilization effect: on entering the TS the free electron pair on the nucleophile moves away from the nucleus, causing a partial positive charge which can be stabilized by an adjacent lone pair as for ...

  9. Azide - Wikipedia

    en.wikipedia.org/wiki/Azide

    However, it has the disadvantage to be prone to trigger unexpected and undesirable side reactions that can jeopardize the experimental results. Indeed, the azide anion is a nucleophile and a redox-active species. Being prone to disproportionation, it can behave both as an oxidizing and as a reducing agent. Therefore, it is susceptible to ...