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Zum basenkatalysierten H/D‐Austausch des acetylenischen Wasserstoffatoms in aromatischen Alkinylverbindungen
Author(s) -
Kramis Jost,
Hansen HansJürgen
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600504
Subject(s) - chemistry , pyrrolidine , medicinal chemistry , stereochemistry
On the Base‐Catalysed H/D‐Exchange of the Acetylenic Hydrogen Atom in Aromatic Alkynyl Compounds H/D‐exchange rates for a number of compounds of the general type 1 (X = p ‐CH 3 O, m ‐CH 3 O, p ‐CF 3 , m ‐CF 3 , p ‐CH 3 , p ‐Cl, H; Z O, NH, CH 2 ) were determined in N ‐methyl‐pyrrolidine (NMP)/D 2 O mixtures at 25° (see Table 1 ). It is shown that the log k values of the H/D‐exchange correlate nicely (r = 0.995) with the chemical shift of the acetylenic proton in 1 . Thus, the H/D‐exchange rate is given by log k (min −1 ) = 2.91 · δ (ppm) ‐ 7.79 for the NMP/D 2 O mixture at 25°.