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

44 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

Fingerprint

Electron affinity
Hydrogen Bonding
Titration
Hydrogen bonds
Nuclear magnetic resonance
Modulation
Association reactions
Electrons
modulation
hydrogen
electron affinity
titration
affinity
Hydrogen
interactions
hydrogen bonds
perturbation
nuclear magnetic resonance
matrices
electrons

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chang, Sung Youn ; Kim, Hung Sop ; Chang, Kyoung Jin ; Jeong, Kyu Sung. / Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents. In: Organic Letters. 2004 ; Vol. 6, No. 2. pp. 181-184.
@article{a47a9ba645b845da955fa4653d8b3904,
title = "Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents",
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.",
author = "Chang, {Sung Youn} and Kim, {Hung Sop} and Chang, {Kyoung Jin} and Jeong, {Kyu Sung}",
year = "2004",
month = "1",
day = "22",
doi = "10.1021/ol035954j",
language = "English",
volume = "6",
pages = "181--184",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "2",

}

Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents. / Chang, Sung Youn; Kim, Hung Sop; Chang, Kyoung Jin; Jeong, Kyu Sung.

In: Organic Letters, Vol. 6, No. 2, 22.01.2004, p. 181-184.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents

AU - Chang, Sung Youn

AU - Kim, Hung Sop

AU - Chang, Kyoung Jin

AU - Jeong, Kyu Sung

PY - 2004/1/22

Y1 - 2004/1/22

N2 - (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.

AB - (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.

UR - http://www.scopus.com/inward/record.url?scp=0842306890&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0842306890&partnerID=8YFLogxK

U2 - 10.1021/ol035954j

DO - 10.1021/ol035954j

M3 - Article

C2 - 14723523

AN - SCOPUS:0842306890

VL - 6

SP - 181

EP - 184

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 2

ER -