From reactants to products via simple hydrogen-bonding networks: Information transmission in chemical reactions
| العنوان: | From reactants to products via simple hydrogen-bonding networks: Information transmission in chemical reactions |
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| المؤلفون: | Aden Murphy, Giuseppe Brancato, Francesco Zerbetto, Jenny K. Y. Wong, Frédéric Coutrot, David A. Leigh |
| المساهمون: | University of Edinburgh, Brancato, Giuseppe, Coutrot, F, Leigh, Da, Murphy, A, Wong, Jky, Zerbetto, F. |
| المصدر: | Proceedings of the National Academy of Sciences of the United States of America Proceedings of the National Academy of Sciences of the United States of America, National Academy of Sciences, 2002, 99 (8), pp.4967-4971. ⟨10.1073/pnas.072695799⟩ |
| بيانات النشر: | HAL CCSD, 2002. |
| سنة النشر: | 2002 |
| مصطلحات موضوعية: | Models, Molecular, Rotaxane, Rotaxanes, Macromolecular Substances, Supramolecular chemistry, Glycine, Sequence (biology), 010402 general chemistry, 01 natural sciences, Chemical reaction, Distortion, Organic chemistry, ComputingMilieux_MISCELLANEOUS, Multidisciplinary, 010405 organic chemistry, Chemistry, Hydrogen bond, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Final product, Hydrogen Bonding, Models, Theoretical, Symmetry (physics), 0104 chemical sciences, Models, Chemical, Chemical physics, Physical Sciences |
| الوصف: | The transmission of information is ubiquitous in nature and often occurs through supramolecular hydrogen bonding processes. Here we report that there is a remarkable correlation during synthesis between the efficiency of the hydrogen-bond-directed assembly of peptide-based [2]rotaxanes and the symmetry distortion of the macrocycle in the structure of the final product. It transpires that the ability of the flexible macrocycle-precursor to wrap around an unsymmetrical hydrogen bonding template affects both the reaction yield and a quantifiable measure of the symmetry distortion of the macrocycle in the product. When the yields of peptide rotaxane-forming reactions are high, so is the symmetry distortion in the macrocycle; when the yields are low, indicating a poor fit between the components, the macrocycle symmetry is relatively unaffected by the thread. Thus during a synthetic sequence, as in complex biological assembly processes, hydrogen bonding can code and transmit “information”—in this case a distortion from symmetry—between chemical entities by means of a supramolecularly driven multicomponent assembly process. If this phenomenon is general, it could have far reaching consequences for the use of supramolecular-directed reactions in organic chemistry. |
| اللغة: | English |
| تدمد: | 0027-8424 1091-6490 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2d148d30f40c5ebbc2e3d7c9d0334678Test https://hal.archives-ouvertes.fr/hal-03247591Test |
| حقوق: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....2d148d30f40c5ebbc2e3d7c9d0334678 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 00278424 10916490 |
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