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Insight into the reaction between a primary amine and a cavitand with an introverted aldehyde group: an enzyme-like mechanism.

Abstract
Density functional theory investigations reveal that a cavitand with an introverted aldehyde group not only provides the host-guest interaction for preorganizing the substrate and stabilizing the hemiaminal intermediate, but also acts as an acid/base catalyst in the subsequent dehydration step in its reaction with a primary amine.
AuthorsLina Xu, Shugui Hua, Shuhua Li
JournalChemical communications (Cambridge, England) (Chem Commun (Camb)) Vol. 49 Issue 15 Pg. 1542-4 (Feb 21 2013) ISSN: 1364-548X [Electronic] England
PMID23325093 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Aldehydes
  • Amines
  • Enzymes
  • Ethers, Cyclic
  • Gases
  • Resorcinols
  • cavitand
Topics
  • Aldehydes
  • Amines (chemistry)
  • Catalysis
  • Enzymes (chemistry, metabolism)
  • Ethers, Cyclic (chemistry)
  • Gases (chemistry)
  • Hydrogen Bonding
  • Resorcinols (chemistry)
  • Thermodynamics

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