Highly Effective Hydrogen‐Bonding Receptors for Guanine Derivatives

Thomas W. Bell; Zheng Hou; Steven C. Zimmerman; Paul A. Thiessen

doi:10.1002/anie.199521631

Highly Effective Hydrogen‐Bonding Receptors for Guanine Derivatives

Thomas W. Bell, Zheng Hou, Steven C. Zimmerman, Paul A. Thiessen

Chemistry

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

Abstract

In the complexation of neutral organic molecules, preorganization of the receptors can play a crucial role, as studies on a new series of hydrogen‐bonding receptors demonstrate. The receptor shown in the complex on the right binds guanine derivatives in [D₆]DMSO/CDCl₃ (1/4) with a stability constant (K_a) greater than 1.9 × 10⁵ M⁻¹. In comparison, a complex with a more flexible host and the same number of primary hydrogen‐bonding sites is at least 4.1 kcalmol⁻¹ less stable. (Figure Presented.)

Original language	English (US)
Pages (from-to)	2163-2165
Number of pages	3
Journal	Angewandte Chemie International Edition in English
Volume	34
Issue number	19
DOIs	https://doi.org/10.1002/anie.199521631
State	Published - Oct 16 1995

Keywords

Hydrogen bonds
Molecular recognition
Nucleosides

ASJC Scopus subject areas

Chemistry(all)

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10.1002/anie.199521631

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abstract = "In the complexation of neutral organic molecules, preorganization of the receptors can play a crucial role, as studies on a new series of hydrogen‐bonding receptors demonstrate. The receptor shown in the complex on the right binds guanine derivatives in [D6]DMSO/CDCl3 (1/4) with a stability constant (Ka) greater than 1.9 × 105 M−1. In comparison, a complex with a more flexible host and the same number of primary hydrogen‐bonding sites is at least 4.1 kcalmol−1 less stable. (Figure Presented.)",

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N2 - In the complexation of neutral organic molecules, preorganization of the receptors can play a crucial role, as studies on a new series of hydrogen‐bonding receptors demonstrate. The receptor shown in the complex on the right binds guanine derivatives in [D6]DMSO/CDCl3 (1/4) with a stability constant (Ka) greater than 1.9 × 105 M−1. In comparison, a complex with a more flexible host and the same number of primary hydrogen‐bonding sites is at least 4.1 kcalmol−1 less stable. (Figure Presented.)

AB - In the complexation of neutral organic molecules, preorganization of the receptors can play a crucial role, as studies on a new series of hydrogen‐bonding receptors demonstrate. The receptor shown in the complex on the right binds guanine derivatives in [D6]DMSO/CDCl3 (1/4) with a stability constant (Ka) greater than 1.9 × 105 M−1. In comparison, a complex with a more flexible host and the same number of primary hydrogen‐bonding sites is at least 4.1 kcalmol−1 less stable. (Figure Presented.)

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KW - Nucleosides

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Highly Effective Hydrogen‐Bonding Receptors for Guanine Derivatives

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