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 Hamilton

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)8419-8427
Number of pages9
JournalTetrahedron
Volume56
Issue number43
StatePublished - Oct 20 2000

Fingerprint

Hydrogen Bonding
Carboxylic Acids
Self assembly
Hydrogen bonds
Agglomeration
Monomers
Aminopyridines
Derivatives
Mass spectrometry
Mass Spectrometry
Substitution reactions
Nuclear magnetic resonance
Association reactions

Keywords

  • Acylaminopyridine-carboxylic acid
  • Hydrogen bonding
  • Self-assembly

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Hydrogen bonding control of molecular self-assembly : Aggregation behavior of acylaminopyridine-carboxylic acid derivatives in solution and the solid state. / Zafar, Abdullah; Geib, Steven J.; Hamuro, Yoshitomo; Carr, Andrew J.; Hamilton, Andrew.

In: Tetrahedron, Vol. 56, No. 43, 20.10.2000, p. 8419-8427.

Research output: Contribution to journalArticle

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