Hydrogen bonding control of molecular self-assembly: Aggregation behavior of acylaminopyridine-carboxylic acid derivatives in solution and the solid state

Abdullah Zafar; Steven J. Geib; Yoshitomo Hamuro; Andrew J. Carr; Andrew D. Hamilton

doi:10.1016/S0040-4020(00)00733-X

Hydrogen bonding control of molecular self-assembly: Aggregation behavior of acylaminopyridine-carboxylic acid derivatives in solution and the solid state

Abdullah Zafar, Steven J. Geib, Yoshitomo Hamuro, Andrew J. Carr, Andrew D. Hamilton

Chemistry

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

Abstract

In this paper we report the design, synthesis and investigation of a family of acylaminopyridine-carboxylic acid monomers that can aggregate through bidentate hydrogen bonding interactions between the carboxylic acid and the aminopyridine sites. We show that in solution the nature of the aggregate depends on the substitution pattern of the monomer and present evidence from NMR and mass spectrometry that in some cases cyclic association occurs. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	8419-8427
Number of pages	9
Journal	Tetrahedron
Volume	56
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4020(00)00733-X
State	Published - Oct 20 2000

Keywords

Acylaminopyridine-carboxylic acid
Hydrogen bonding
Self-assembly

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00733-X

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title = "Hydrogen bonding control of molecular self-assembly: Aggregation behavior of acylaminopyridine-carboxylic acid derivatives in solution and the solid state",

abstract = "In this paper we report the design, synthesis and investigation of a family of acylaminopyridine-carboxylic acid monomers that can aggregate through bidentate hydrogen bonding interactions between the carboxylic acid and the aminopyridine sites. We show that in solution the nature of the aggregate depends on the substitution pattern of the monomer and present evidence from NMR and mass spectrometry that in some cases cyclic association occurs. (C) 2000 Elsevier Science Ltd.",

keywords = "Acylaminopyridine-carboxylic acid, Hydrogen bonding, Self-assembly",

author = "Abdullah Zafar and Geib, {Steven J.} and Yoshitomo Hamuro and Carr, {Andrew J.} and Hamilton, {Andrew D.}",

note = "Funding Information: This work was supported by a grant from the National Science Foundation.",

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T1 - Hydrogen bonding control of molecular self-assembly

T2 - Aggregation behavior of acylaminopyridine-carboxylic acid derivatives in solution and the solid state

AU - Zafar, Abdullah

AU - Geib, Steven J.

AU - Hamuro, Yoshitomo

AU - Carr, Andrew J.

AU - Hamilton, Andrew D.

N1 - Funding Information: This work was supported by a grant from the National Science Foundation.

PY - 2000/10/20

Y1 - 2000/10/20

N2 - In this paper we report the design, synthesis and investigation of a family of acylaminopyridine-carboxylic acid monomers that can aggregate through bidentate hydrogen bonding interactions between the carboxylic acid and the aminopyridine sites. We show that in solution the nature of the aggregate depends on the substitution pattern of the monomer and present evidence from NMR and mass spectrometry that in some cases cyclic association occurs. (C) 2000 Elsevier Science Ltd.

AB - In this paper we report the design, synthesis and investigation of a family of acylaminopyridine-carboxylic acid monomers that can aggregate through bidentate hydrogen bonding interactions between the carboxylic acid and the aminopyridine sites. We show that in solution the nature of the aggregate depends on the substitution pattern of the monomer and present evidence from NMR and mass spectrometry that in some cases cyclic association occurs. (C) 2000 Elsevier Science Ltd.

KW - Acylaminopyridine-carboxylic acid

KW - Hydrogen bonding

KW - Self-assembly

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SN - 0040-4020

VL - 56

SP - 8419

EP - 8427

JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

Hydrogen bonding control of molecular self-assembly: Aggregation behavior of acylaminopyridine-carboxylic acid derivatives in solution and the solid state

Abstract

Keywords

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