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Theoretical Models and Experimental Data for Reactions between Water and Protonated Alcohols: Substitution and Elimination Mechanisms
Author(s) -
Uggerud Einar,
BacheAndreassen Lihn
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990604)5:6<1917::aid-chem1917>3.0.co;2-r
Subject(s) - sn2 reaction , steric effects , protonation , substitution (logic) , chemistry , reactivity (psychology) , nucleophilic substitution , substitution reaction , nucleophile , computational chemistry , medicinal chemistry , organic chemistry , catalysis , philosophy , medicine , ion , alternative medicine , pathology , linguistics
The reactivity order for S N 2 water substitution of protonated alcohols in the gas phase is significantly different from that normally found for stronger nucleophiles (the figure shows a transition state). This finding challenges the universal validity of the concept “steric hindrance”.