Anion binding induces helicity in a hydrogen-bonding receptor: crystal structure of a 2,6-bis(anilinoethynyl)pyridinium chloride

Charles A. Johnson; Orion B. Berryman; Aaron C. Sather; Lev N. Zakharov; Michael M. Haley; Darren W. Johnson

doi:10.1021/cg900674p

Anion binding induces helicity in a hydrogen-bonding receptor: crystal structure of a 2,6-bis(anilinoethynyl)pyridinium chloride

Charles A. Johnson, Orion B. Berryman, Aaron C. Sather, Lev N. Zakharov, Michael M. Haley, Darren W. Johnson

Chemistry and Biochemistry

University of Oregon

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

26 Scopus citations

Abstract

The synthesis and solid-state of 2,6-bis(anilinoethynyl)pyridine amide 1 is presented. Neutral receptor 1 forms a polymeric chain through hydrogen bonds and π stacking in the solid state. Upon protonation, receptor 1 undergoes significant conformational rearrangement to hydrogen bond to Cl^-, forming a helix (Hl⁺Cl^-). This rare example of anion-induced helicity is detailed in the solid state and initial solution studies are presented.

Original language	English
Pages (from-to)	4247-4249
Number of pages	3
Journal	Crystal Growth and Design
Volume	9
Issue number	10
DOIs	https://doi.org/10.1021/cg900674p
State	Published - Oct 7 2009

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abstract = "The synthesis and solid-state of 2,6-bis(anilinoethynyl)pyridine amide 1 is presented. Neutral receptor 1 forms a polymeric chain through hydrogen bonds and π stacking in the solid state. Upon protonation, receptor 1 undergoes significant conformational rearrangement to hydrogen bond to Cl-, forming a helix (Hl+Cl-). This rare example of anion-induced helicity is detailed in the solid state and initial solution studies are presented.",

author = "Johnson, \{Charles A.\} and Berryman, \{Orion B.\} and Sather, \{Aaron C.\} and Zakharov, \{Lev N.\} and Haley, \{Michael M.\} and Johnson, \{Darren W.\}",

year = "2009",

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T1 - Anion binding induces helicity in a hydrogen-bonding receptor

T2 - crystal structure of a 2,6-bis(anilinoethynyl)pyridinium chloride

AU - Johnson, Charles A.

AU - Berryman, Orion B.

AU - Sather, Aaron C.

AU - Zakharov, Lev N.

AU - Haley, Michael M.

AU - Johnson, Darren W.

PY - 2009/10/7

Y1 - 2009/10/7

N2 - The synthesis and solid-state of 2,6-bis(anilinoethynyl)pyridine amide 1 is presented. Neutral receptor 1 forms a polymeric chain through hydrogen bonds and π stacking in the solid state. Upon protonation, receptor 1 undergoes significant conformational rearrangement to hydrogen bond to Cl-, forming a helix (Hl+Cl-). This rare example of anion-induced helicity is detailed in the solid state and initial solution studies are presented.

AB - The synthesis and solid-state of 2,6-bis(anilinoethynyl)pyridine amide 1 is presented. Neutral receptor 1 forms a polymeric chain through hydrogen bonds and π stacking in the solid state. Upon protonation, receptor 1 undergoes significant conformational rearrangement to hydrogen bond to Cl-, forming a helix (Hl+Cl-). This rare example of anion-induced helicity is detailed in the solid state and initial solution studies are presented.

UR - https://www.scopus.com/pages/publications/70350233216

U2 - 10.1021/cg900674p

DO - 10.1021/cg900674p

M3 - Article

AN - SCOPUS:70350233216

SN - 1528-7483

VL - 9

SP - 4247

EP - 4249

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 10

ER -

Anion binding induces helicity in a hydrogen-bonding receptor: crystal structure of a 2,6-bis(anilinoethynyl)pyridinium chloride

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