Tetrahedral carbonyl addition compound (original) (raw)
Als tetraedrisches Zwischenprodukt, auch tetraedrisches Intermediat (TIM nach Frank Glorius) wird ein in organischen Synthesen entstehendes Zwischenprodukt bezeichnet, bei dem das relevante Kohlenstoffatom tetraedrisch umgeben ist. Somit ist eine Racemisierung im folgenden Reaktionsschritt ausgeschlossen.
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| dbo:abstract | Als tetraedrisches Zwischenprodukt, auch tetraedrisches Intermediat (TIM nach Frank Glorius) wird ein in organischen Synthesen entstehendes Zwischenprodukt bezeichnet, bei dem das relevante Kohlenstoffatom tetraedrisch umgeben ist. Somit ist eine Racemisierung im folgenden Reaktionsschritt ausgeschlossen. (de) A tetrahedral intermediate is a reaction intermediate in which the bond arrangement around an initially double-bonded carbon atom has been transformed from trigonal to tetrahedral. Tetrahedral intermediates result from nucleophilic addition to a carbonyl group. The stability of tetrahedral intermediate depends on the ability of the groups attached to the new tetrahedral carbon atom to leave with the negative charge. Tetrahedral intermediates are very significant in organic syntheses and biological systems as a key intermediate in esterification, transesterification, ester hydrolysis, formation and hydrolysis of amides and peptides, hydride reductions, and other chemical reactions. (en) 四面体型中間体（しめんたいがたちゅうかんたい）もしくは四面体中間体（英語: Tetrahedral intermediate、TI）は炭素原子の周りで結合の組み換えが起こり、二重結合を持つ平面三角形の炭素が四面体型のsp3炭素に変わるときに生成する反応中間体である。四面体型中間体はカルボニル基への求核付加によって炭素-酸素結合のπ結合が切れて生成する。四面体型中間体の安定性は新しいsp3炭素に結合している、負電荷を持った脱離基の脱離能に依存する。もし元から結合していた基と新しくカルボニルに結合する基の両方が電気的に陰性である場合、四面体型中間体は不安定である。四面体型中間体はエステル化やエステル交換反応、エステルの加水分解、アミドやペプチドの合成や加水分解、ヒドリド還元などの反応で鍵となる中間体であるため、これらの反応を扱う有機合成やできわめて重要である。 (ja) Um intermediário tetraédrico pode ser definido como um intermediário reativo formado a partir de uma adição nucleofílica ao átomo de carbono de uma carbonila, o que faz com que o carbono que estava arranjado inicialmente numa geometria trigonal plana (hibridização sp²) adquira uma geometria tetraédrica (hibridização sp3). A estabilidade do intermediário tetraédrico está relacionada diretamente à capacidade dos grupos ligados ao átomo de carbono tetraédrico em dispersar a carga negativa. A formação de intermediários tetraédricos pode ser observada numa grande gama de reações em síntese orgânica e sistema biológicos, como, por exemplo, transesterificação, esterificação, hidrólise de ésteres, amida e pepitídeos. (pt) |
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| rdfs:comment | Als tetraedrisches Zwischenprodukt, auch tetraedrisches Intermediat (TIM nach Frank Glorius) wird ein in organischen Synthesen entstehendes Zwischenprodukt bezeichnet, bei dem das relevante Kohlenstoffatom tetraedrisch umgeben ist. Somit ist eine Racemisierung im folgenden Reaktionsschritt ausgeschlossen. (de) A tetrahedral intermediate is a reaction intermediate in which the bond arrangement around an initially double-bonded carbon atom has been transformed from trigonal to tetrahedral. Tetrahedral intermediates result from nucleophilic addition to a carbonyl group. The stability of tetrahedral intermediate depends on the ability of the groups attached to the new tetrahedral carbon atom to leave with the negative charge. Tetrahedral intermediates are very significant in organic syntheses and biological systems as a key intermediate in esterification, transesterification, ester hydrolysis, formation and hydrolysis of amides and peptides, hydride reductions, and other chemical reactions. (en) 四面体型中間体（しめんたいがたちゅうかんたい）もしくは四面体中間体（英語: Tetrahedral intermediate、TI）は炭素原子の周りで結合の組み換えが起こり、二重結合を持つ平面三角形の炭素が四面体型のsp3炭素に変わるときに生成する反応中間体である。四面体型中間体はカルボニル基への求核付加によって炭素-酸素結合のπ結合が切れて生成する。四面体型中間体の安定性は新しいsp3炭素に結合している、負電荷を持った脱離基の脱離能に依存する。もし元から結合していた基と新しくカルボニルに結合する基の両方が電気的に陰性である場合、四面体型中間体は不安定である。四面体型中間体はエステル化やエステル交換反応、エステルの加水分解、アミドやペプチドの合成や加水分解、ヒドリド還元などの反応で鍵となる中間体であるため、これらの反応を扱う有機合成やできわめて重要である。 (ja) Um intermediário tetraédrico pode ser definido como um intermediário reativo formado a partir de uma adição nucleofílica ao átomo de carbono de uma carbonila, o que faz com que o carbono que estava arranjado inicialmente numa geometria trigonal plana (hibridização sp²) adquira uma geometria tetraédrica (hibridização sp3). A estabilidade do intermediário tetraédrico está relacionada diretamente à capacidade dos grupos ligados ao átomo de carbono tetraédrico em dispersar a carga negativa. A formação de intermediários tetraédricos pode ser observada numa grande gama de reações em síntese orgânica e sistema biológicos, como, por exemplo, transesterificação, esterificação, hidrólise de ésteres, amida e pepitídeos. (pt) |
| rdfs:label | Tetraedrisches Zwischenprodukt (de) 四面体型中間体 (ja) Intermediários tetraédricos (pt) Tetrahedral carbonyl addition compound (en) |
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