Premium
The Role of Ring Strain on the Ease of Ring Closure of Bifunctional Chain Molecules
Author(s) -
Galli Carlo,
Mandolini Luigi
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:18<3117::aid-ejoc3117>3.0.co;2-5
Subject(s) - chemistry , ring strain , intramolecular force , ring (chemistry) , bifunctional , molecule , computational chemistry , strain (injury) , crystallography , stereochemistry , catalysis , organic chemistry , medicine
The role of ring strain on the ease of ring formation over a wide range of ring sizes is discussed on the basis of a comparison of transition state versus product‐ring strain energies. A general procedure is illustrated for the assessment of transition‐state strain energies, based on experimental effective molarities ( EM s) and an extra‐thermodynamic treatment of entropy data for ring closure. It is found that the ring product is a good model of the transition state of cyclisation for all but the shortest chains. Our earlier interpretation of this remarkable lack of correspondence between transition state and product‐ring strain energies in intramolecular nucleophilic substitutions of the very short chains, is compared with the results of recent theoretical calculations.