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Effect of the substituents on the conformational behavior of five‐membered rings: Application to the cis‐ and trans‐2,5‐dimethoxytetrahydrofuran
Author(s) -
Diez Ernesto,
Palma Jesús,
SanFabián Jesús,
Guilleme Joaquin,
Esteban Angel L.,
Galache Maria P.
Publication year - 1988
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540090302
Subject(s) - vicinal , chemistry , ring (chemistry) , coupling constant , computational chemistry , stereochemistry , spin (aerodynamics) , proton , proton spin crisis , force field (fiction) , crystallography , organic chemistry , thermodynamics , quantum mechanics , physics
A model is proposed which assumes that the pseudorotational potential in five‐membered rings is given by the combination of contributions from the unsubstituted ring, from the individual substituents and from interactions between pairs of substituents. The application of this model to the potentials calculated by the MM2 force field for the cis and trans ‐2,5‐dimethoxytetrahydrofuran shows that the contributions from the individual substituents explain the main features of the potentials of these disubstituted rings. The pseudorotational analysis from vicinal proton spin‐spin coupling constants 3 J HH confirms the realibility of the MM2 potentials.