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Alkylating properties of phosphate esters. 4. Medium effects on methylation of pyridines by trimethyl phosphate
Author(s) -
Modro A. M.,
Modro T. A.
Publication year - 1989
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610020503
Subject(s) - chemistry , phosphate , solvent , nucleophile , trimethyl phosphate , pyridine , chloroform , substrate (aquarium) , methylation , ring (chemistry) , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , dna , biochemistry , oceanography , geology
The rates of N ‐methylation of pyridine and its ring‐substituted derivatives by trimethyl phosphate were measured in D 2 O and in CDCl 3 . Relative rates, together with the solvent activity coefficients of substrates for the transfer form chloroform to water, were used for determining the solvent activity coefficients of the activated complexes for this S N 2 reaction. The results indicate early activated complexes for all pyridines, with the most nucleophilic substrate showing the most reactant‐like activated complex.