molecular modelling of guanidinium/carboylate interaction



 Dear Netters!
 A biochemist, who uses Insight/Discover and Macromodel came along
 with an interesting question concerning molecular modelling. I pass
 it on to the net, hoping to find experts in this field. Here is
 the problem:
 The interaction of a guanidinium function and a carboxylate fnc
 was modelled using the software cited above (I do not know, which
 force fields they used).
                 N---H - - - O
                /             \
               /               \
      R---N---C +           -   C---R
               \               /
                \             /
                 N---H - - - O
 In either case they did not obtain a planar geometry. Indeed, the
 COO turns out to be almost perpendicular to the C(NH)2 plane, which
 is not, what one would intuitively assume to be realistic. So what
 might have gone wrong? They don't have any idea, and I (as a new-
 comer to the field of MM) only have some vague assumptions. If
 you have any experience with such systems, please contact me!
 Thank you!
    L. Ackermann
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                           *                                                   *
                           * Dr. Lutz Ackermann                                *
                           *                                                   *
                           * Lehrstuhl fuer Theoretische Chemie (TU Munich)    *
                           * Lichtenbergstr. 4                                 *
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                           * Germany                                           *
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                           * e-mail   ackerman()at()theo1.theochem.tu-muenchen.de
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