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Alcohols and Ethers (LS)

Alcohols and Ethers (LS) - Crown Ethers Introduction to...

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Lecture Supplement: Crown Ethers: Introduction to Molecular Recognition 5 Crown Ethers: Introduction to Molecular Recognition Molecular recognition: Weak, reversible and selective binding between two molecules. Association based on shape, size, charge, hydrogen bonding, etc. Broad significance, especially biological chemistry Enzyme - substrate selectivity Nucleic acid - protein interactions DNA base pairing Exploration example: Crown ethers - Large ring polyethers O O O O O O O O O O O O O O O 12-crown-4 ring size shape oxygens 15-crown-5 18-crown-6 Shape: Page 413, Brown & Foote Cavity is electron rich (oxygen lone pairs); can form complex with a cation Exterior is hydrophobic (hydrophobic blanket; inverted micelle) 12-Crown 4: Lighter grey = higher electron density 12-Crown-4/Li + complex Color pictures: web.chem.ucla.edu/~harding/crownethers.html
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6 Lecture Supplement: Crown Ethers: Introduction to Molecular Recognition Cavity size proportional to ring size, so crown ethers display selectivity in
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