Reactions of triarylmethyl carbocations with hydride donors and other nucleophiles

✍ Scribed by C.A. Bunton; S.K. Huang; C.H. Paik

• Book ID: 104212869
• Publisher: Elsevier Science
• Year: 1976
• Tongue: French
• Weight: 233 KB
• Volume: 17
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71279-2

✦ Synopsis

The N+ scale of nucleophilicity, evaluated from reactivities toward carbocationa, was initially interpreted in term of anionic desolvati0n.l The scale also fits diaeonium ion capture and deacylations, provided that allowauce is made for partitioning of tetrahedral intenuediatee.

However, nucleophilicities, especially towards esters, have often been correlated with basicity,2 and for different series of reagents they have been rationalized uaiug the hard-soft principle,a but the BucceBs of the N, scale illustrates the importance of deaolvation of anionic, and by implication, nonionic, nucleoprules, =, amines.