| Proton grease: an acid accelerated molecular rotor. | |
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MedLine Citation:
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PMID: 22320172 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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A molecular rotor was designed that rotates seven orders of magnitude faster upon protonation. The quinoline rotor is based on a rigid N-arylimide framework that displays restricted rotation due to the severe steric interaction between the imide carbonyls and the quinoline nitrogen. At rt (23 °C), the rotor rotates slowly (t1/2 = 26 min, ΔG‡ = 22.2 kcal/mol). However, upon addition of 3.5 equiv of acid the rotor rotates rapidly (t1/2 = 2.0 x 10-4 s, ΔG‡ = 12.9 kcal/mol). Mechanistic studies show that this dramatic acid catalyzed change is due to stabilization of the planar transition state by the formation of an intramolecular hydrogen bond between the protonated quinoline nitrogen (N+-H) and an imide carbonyl (O=C). The acid catalyzed acceleration is reversible and can be stopped by addition of base. |
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Authors:
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Brent E Dial; Perry J Pellechia; Mark D Smith; Ken Daniel Shimizu |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-2-9 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: - ISSN: 1520-5126 ISO Abbreviation: - Publication Date: 2012 Feb |
Date Detail:
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Created Date: 2012-2-10 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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