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Energetic analyses of chair and boat conformations of maleimide substituted cyclohexane derivatives
Author(s) -
Remmert Sarah,
Parish Carol
Publication year - 2008
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.21125
Subject(s) - maleimide , cyclohexane , chemistry , solvent , force field (fiction) , quantum chemical , computational chemistry , polymer chemistry , molecule , organic chemistry , computer science , artificial intelligence
An analysis of the conformational preferences of two maleimide substituted cyclohexane derivatives proposed as scaffolds for HIV‐1 fusion inhibitors is presented. Hybrid Low Mode‐Monte Carlo (1:1) conformational searches using seven different force fields were performed in combination with the GBSA(water) solvent model. Low energy structures identified in this way were subjected to geometry optimization on the B3LYP/6‐31G** surface. Solvent effects were included in the quantum calculation using the self‐consistent reaction field model for water. Quantum results indicate that the 1,3,5‐maleimide functionalized 1,3,5‐methyl cyclohexane is more stable in the boat conformation, whereas 1,3,5‐maleimide functionalized cyclohexane adopts the expected chair conformation with equatorial arms. None of the force fields studied was able to predict the unexpected preference for the boat conformation of 1,3,5‐maleimide functionalized 1,3,5‐methyl cyclohexane. Comparison of low energy and experimental structures was also performed. © 2008 Wiley Periodicals, Inc. J Comput Chem, 2009