Premium
Consequences of Strain for the Structure of Aliphatic Molecules
Author(s) -
Rüchardt Christoph,
Beckhaus HansDieter
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198505293
Subject(s) - conformational isomerism , force field (fiction) , molecule , molecular geometry , deformation (meteorology) , computational chemistry , strain (injury) , bond length , chemistry , work (physics) , crystallography , materials science , thermodynamics , physics , organic chemistry , composite material , quantum mechanics , medicine
The chemist is accustomed to deriving structures and preferred conformations of organic compounds from rigid molecular models and standard values for bond lengths, bond angles, and torsional profiles. In the case of strained compounds, this rigid structural model has to be abandoned and replaced by a flexible one which takes individual conditions of strain into consideration. It is shown, on the basis of new experimental structure data, that the force field method is suitable and highly reliable for the calculation of structural parameters and preferred conformations of strained compounds. It is, therefore, capable of replacing the rigid molecular model. Furthermore, the systematic analysis of strain induced angle and bond deformation gives a new pivot for the development of a qualitative discussion of deformation in strained molecules and hence for improved conformational analysis. — In the course of this work we were able to isolate two rotamers of D,L ‐3,4‐di(1‐adamantyl)‐2,2,5,5‐tetramethylhexane; this is the first isolation of a rotamer pair of an aliphatic hydrocarbon.