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Synthesis and Conformational Analysis of Bis(1,3‐dioxan‐5‐yl)ethane Derivatives
Author(s) -
Hoffmann Reinhard W.,
Menzel Karsten,
Harms Klaus
Publication year - 2002
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(200208)2002:15<2603::aid-ejoc2603>3.0.co;2-#
Subject(s) - chemistry , computational chemistry , stereochemistry , combinatorial chemistry , medicinal chemistry
Bis(1,3‐dioxan‐5‐yl)ethanes 4 , 30 , 32 , and 33 were synthesized in order to verify the high conformational preferences of their flexible backbones predicted by force‐field calculations. Conformational analysis based on 3 J H,H coupling constants gave results different from expectations based on the force‐field calculations. The MM3* force‐field of MACROMODEL was apparently not parametrized suitably to deal with the double‐ gauche interactions occurring along the backbones of compounds 30 , 32 , and 33 . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)