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Divinyl selenide: conformational study and stereochemical behavior of its 77 Se 1 H spin–spin coupling constants
Author(s) -
Rusakov Yury Yu.,
Krivdin Leonid B.,
Istomitalia V.,
Potapov Vladimir A.,
Amosova Svetlana V.
Publication year - 2008
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2291
Subject(s) - chemistry , selenide , conformational isomerism , coupling constant , spin (aerodynamics) , crystallography , computational chemistry , stereochemistry , molecule , thermodynamics , selenium , organic chemistry , physics , particle physics
Theoretical energy‐based conformational analysis of divinyl selenide performed at the MP2/6‐311G** level is substantiated by the second‐order polarization propagator approach (SOPPA) calculations and experimental measurements of its 77 Se 1 H spin–spin coupling constants, demonstrating marked stereochemical behavior in respect of the internal rotation of both vinyl groups around the SeC bonds. Based on these data, divinyl selenide is shown to exist in an equilibrium mixture of three nonplanar conformers: one the preferred syn‐s‐cis‐s‐trans and two minor anti‐s‐trans‐s‐trans and syn‐s‐trans‐s‐trans forms. Copyright © 2008 John Wiley & Sons, Ltd.