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Nitrogen‐15 Kinetic Isotope Effects in the Menschutkin‐Type Reaction of Benzyl Benzenesulfonates with N,N ‐Dimethylanilines
Author(s) -
Ando Takashi,
Yamataka Hiroshi,
Wada Eitaro
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500119
Subject(s) - chemistry , kinetic isotope effect , reactivity (psychology) , nitrogen , acetone , kinetic energy , isotope , medicinal chemistry , selectivity , isotopes of nitrogen , organic chemistry , catalysis , deuterium , medicine , physics , alternative medicine , pathology , quantum mechanics
Nitrogen‐15 kinetic isotope effects were measured for the Menschutkin‐type reaction of Z‐substituted benzyl X‐substituted benzenesulfonates with Y‐substituted N,N ‐dimethylanilines (Eq. 1) in acetone at 35°C. The values of 14 k / 15 k for six combinations of X, Y, and Z fell in the range of 1.002–1.004. These small and almost constant nitrogen isotope effects are in contrast to the large and extensively varying carbon‐14 and small but distinctly changing α‐tritium isotope effects observed for this reaction series. The results are discussed in connection with the reactivity–selectivity relationships.