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

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

49 Scopus citations

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

Keywords

hydrogen bonds
molecular recognition
nucleosides

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.199521631

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title = "Highly Effective Hydrogen‐Bonding Receptors for Guanine Derivatives",

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.)",

keywords = "hydrogen bonds, molecular recognition, nucleosides",

author = "Bell, {Thomas W.} and Zheng Hou and Zimmerman, {Steven C.} and Thiessen, {Paul A.}",

year = "1995",

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doi = "10.1002/anie.199521631",

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T1 - Highly Effective Hydrogen‐Bonding Receptors for Guanine Derivatives

AU - Bell, Thomas W.

AU - Hou, Zheng

AU - Zimmerman, Steven C.

AU - Thiessen, Paul A.

PY - 1995/10/16

Y1 - 1995/10/16

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.)

KW - hydrogen bonds

KW - molecular recognition

KW - nucleosides

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U2 - 10.1002/anie.199521631

DO - 10.1002/anie.199521631

M3 - Article

AN - SCOPUS:33748228056

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VL - 34

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 19

ER -

Highly Effective Hydrogen‐Bonding Receptors for Guanine Derivatives

Abstract

Keywords

ASJC Scopus subject areas

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