4,15-Dimethyl-7,12-diazo­niatri­cyclo­[10.4.0.0 2,7 ]hexa­deca-1(12),2,4,6,13,15-hexa­ene dibromide monohydrate

Edward J. Behrman; Alexandar L. Hansen; Chunhua Yuan; Sean Parkin

doi:10.1107/S2056989020011147

4,15-Dimethyl-7,12-diazoniatricyclo[10.4.0.0 2,7 ]hexadeca-1(12),2,4,6,13,15-hexaene dibromide monohydrate

Edward J. Behrman, Alexandar L. Hansen, Chunhua Yuan, Sean Parkin

Chemistry

Producción científica: Article › revisión exhaustiva

Resumen

The title compound, C 16 H 20 N 2 2+ ·2Br - ·H 2 O (1) is a member of the class of compounds called viologens. Viologens are quaternary salts of dipyridyls and are especially useful as redox indicators as a result of their large negative one-electron reduction potentials. Compound 1 consists of a dication composed of a pair of 4-methylpyridine rings mutually joined at the 2-position, with a dihedral angle between the pyridine rings of 62.35 (4)°. In addition, the rings are tethered via the pyridine nitrogen atoms by a tetramethylene bridge. Charge balance is provided by a pair of bromide anions, which are hydrogen bonded to a single water molecule [D O⋯Br = 3.3670 (15) and 3.3856 (15) Å]. The crystal structure of 1, details of an improved synthesis, and a full analysis of its NMR spectra are presented.

Idioma original	English
Páginas (desde-hasta)	1467-1471
Número de páginas	5
Publicación	Acta Crystallographica Section E: Crystallographic Communications
Volumen	76
DOI	https://doi.org/10.1107/S2056989020011147
Estado	Published - sept 1 2020

Nota bibliográfica

Publisher Copyright:
© 2020 International Union of Crystallography. All rights reserved.

Financiación

Funding for this research was provided by: NSF (grant No. CHE1625732 to Sean Parkin). The D8 Venture diffractometer was funded by the NSF (MRI CHE1625732), and by the University of Kentucky.

Financiadores	Número del financiador
National Science Foundation (NSF)	CHE1625732, MRI CHE1625732
University of Kentucky

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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title = "4,15-Dimethyl-7,12-diazoniatricyclo[10.4.0.0 2,7 ]hexadeca-1(12),2,4,6,13,15-hexaene dibromide monohydrate",

abstract = "The title compound, C 16 H 20 N 2 2+ ·2Br - ·H 2 O (1) is a member of the class of compounds called viologens. Viologens are quaternary salts of dipyridyls and are especially useful as redox indicators as a result of their large negative one-electron reduction potentials. Compound 1 consists of a dication composed of a pair of 4-methylpyridine rings mutually joined at the 2-position, with a dihedral angle between the pyridine rings of 62.35 (4)°. In addition, the rings are tethered via the pyridine nitrogen atoms by a tetramethylene bridge. Charge balance is provided by a pair of bromide anions, which are hydrogen bonded to a single water molecule [D O⋯Br = 3.3670 (15) and 3.3856 (15) {\AA}]. The crystal structure of 1, details of an improved synthesis, and a full analysis of its NMR spectra are presented.",

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AU - Behrman, Edward J.

AU - Hansen, Alexandar L.

AU - Yuan, Chunhua

AU - Parkin, Sean

PY - 2020/9/1

Y1 - 2020/9/1

N2 - The title compound, C 16 H 20 N 2 2+ ·2Br - ·H 2 O (1) is a member of the class of compounds called viologens. Viologens are quaternary salts of dipyridyls and are especially useful as redox indicators as a result of their large negative one-electron reduction potentials. Compound 1 consists of a dication composed of a pair of 4-methylpyridine rings mutually joined at the 2-position, with a dihedral angle between the pyridine rings of 62.35 (4)°. In addition, the rings are tethered via the pyridine nitrogen atoms by a tetramethylene bridge. Charge balance is provided by a pair of bromide anions, which are hydrogen bonded to a single water molecule [D O⋯Br = 3.3670 (15) and 3.3856 (15) Å]. The crystal structure of 1, details of an improved synthesis, and a full analysis of its NMR spectra are presented.

AB - The title compound, C 16 H 20 N 2 2+ ·2Br - ·H 2 O (1) is a member of the class of compounds called viologens. Viologens are quaternary salts of dipyridyls and are especially useful as redox indicators as a result of their large negative one-electron reduction potentials. Compound 1 consists of a dication composed of a pair of 4-methylpyridine rings mutually joined at the 2-position, with a dihedral angle between the pyridine rings of 62.35 (4)°. In addition, the rings are tethered via the pyridine nitrogen atoms by a tetramethylene bridge. Charge balance is provided by a pair of bromide anions, which are hydrogen bonded to a single water molecule [D O⋯Br = 3.3670 (15) and 3.3856 (15) Å]. The crystal structure of 1, details of an improved synthesis, and a full analysis of its NMR spectra are presented.

KW - atropisomer

KW - crystal structure

KW - synthesis

KW - viologen

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