Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents

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

doi:10.1021/ol035954j

Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

48 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 language	English
Pages (from-to)	181-184
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	2
DOIs	https://doi.org/10.1021/ol035954j
Publication status	Published - 2004 Jan 22

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol035954j

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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",

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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.

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Efficient Modulation of Hydrogen-Bonding Interactions by Remote Substituents

Abstract

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