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neighbouring group participation
Neighbouring group participation (NGP) (also known as anchimeric assistance) in organic chemistry has been defined by IUPAC as the interaction of a reaction centre with a lone pair of electrons in an atom or the electrons present in a sigma bond or pi bond . When NGP is in operation it is normal for the reaction rate to be increased. It is also possible for the stereochemistry of the reaction to be abnormal (or unexpected) when compared with a ''normal'' reaction. While it is possible for neighbouring groups to influence many reactions in organic chemistry (''e.g.'' the reaction of a diene such as 1,3-cyclohexadiene with maleic anhydride normally gives the endo isomer because of a secondary effect ) this page is limited to neighbouring group effects seen with carbocations and SN2 reactions.
==NGP by heteroatom lone pairs ==
A classic example of NGP is the reaction of a sulfur or nitrogen mustard with a nucleophile, the rate of reaction is much higher for the sulfur mustard and a nucleophile than it would be for a primary alkyl chloride without a heteroatom.
In sugar chemistry anchimeric assistance is an example of NGP.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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