Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents

Sung Youn Chang, Hung Sop Kim, Kyoung Jin Chang, Kyu Sung Jeong

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

(Matrix presented) A series of tetralactam macrocycles having different substituents were prepared, and their binding affinities for an adipamide guest were investigated in CDCl3 by 1H NMR titrations. The association constants strongly depend on the substituents, varying up to ΔΔG = 3.4 kcal/mol; electron-donating substituents (OMe, NMe 2) decrease the binding affinity, while electron-withdrawing groups (Cl, NO2) increase it. These large substituent effects have been rationalized by secondary repulsions and partial perturbations of intramolecular hydrogen bonds.

Original languageEnglish
Pages (from-to)181-184
Number of pages4
JournalOrganic Letters
Volume6
Issue number2
DOIs
Publication statusPublished - 2004 Jan 22

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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