X‐Ray Structure Analyses of syn/anti‐Conformers of N‐Furfuroyl‐, N‐Benzoyl‐, and N‐Picolinoyl‐Substituted (2R)‐Bornane‐10,2‐sultam Derivatives |
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| Authors: | Karolina Koszewska Anna Piątek Christian Chapuis Janusz Jurczak |
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| Affiliation: | 1. Department of Chemistry, University of Warsaw, Pasteura 1, PL‐02‐093 Warsaw;2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, PL‐01‐224 Warsaw, (phone: +41?22?780?36?10;3. fax: +41?22?780?33?34;4. phone: +48?22?632?05?78;5. fax +48?22?632?66?81);6. Present address: Firmenich SA, Corporate R&D Division, P.O. Box 239, CH‐1211 Geneva 8. |
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| Abstract: | The synthesis and the X‐ray structure of the three new N‐(arylcarbonyl)‐substituted derivatives 2a – 2c of (2R)‐bornane‐10,2‐sultam are presented and discussed. Direct comparison of the solid‐state analyses shows that the dipole‐directed SO2/C?O anti‐/syn‐conformations may be very sensitive to weak electronic/electrostatic repulsions of the heteroatom lone pairs. The optimum interactions are reached when the lone pair of the β‐positioned heteroatom is oriented in the O(3)?C(11)? N(1) plane. Such rare syn‐conformations may be observed with at least up to 1.8 kcal/mol higher energy as compared to their ground states. Additionally, these anti/syn‐conformations are also very sensitive to external influences such as, for example, the crystal‐packing forces. |
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| Keywords: | X‐Ray crystallography (2R)‐Bornane‐10,2‐sultam derivatives |
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