A purple odyssey: synthesis and structure of 3-amino-4-hy­dr­oxy-6-oxo­cyclo­hexa-2,4-dien-1-iminium chloride monohydrate

William T. A. Harrison; M. John Plater

doi:10.1107/S2056989016005107

A purple odyssey: synthesis and structure of 3-amino-4-hydroxy-6-oxocyclohexa-2,4-dien-1-iminium chloride monohydrate

William T. A. Harrison, M. John Plater

Chemistry

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

1 Citation (Scopus)

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Abstract

In the cation of the title hydrated molecular salt, C6H7N2O2+·Cl-·H2O, the six-membered ring shows unequal bond lengths consistent with delocalization of electrons over two separate 6[pi] systems with single bonds between them. In the crystal, the components are linked by N-H...Cl, N-H...O, O-H...Cl and O-H...O hydrogen bonds, generating double layers propagating in (100).

Original language	English
Pages (from-to)	604-607
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	72
Issue number	5
DOIs	https://doi.org/10.1107/S2056989016005107
Publication status	Published - 1 May 2016

Bibliographical note

Acknowledgements

We thank the EPSRC National Crystallography Service (University of Southampton) for the data collection and the EPSRC National Mass Spectrometry Service (University of Swansea) for the HRMS data.

Keywords

conjugation
anti-aromatic
hydrogen bonds
layered structure
crystal structure

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A purple odyssey: synthesis and structure of 3-amino-4-hydroxy-6-oxocyclohexa-2,4-dien-1-iminium chloride monohydrate
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. http://creativecommons.org/licenses/by/4.0/
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Cite this

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title = "A purple odyssey: synthesis and structure of 3-amino-4-hydroxy-6-oxocyclohexa-2,4-dien-1-iminium chloride monohydrate",

abstract = "In the cation of the title hydrated molecular salt, C6H7N2O2+·Cl-·H2O, the six-membered ring shows unequal bond lengths consistent with delocalization of electrons over two separate 6[pi] systems with single bonds between them. In the crystal, the components are linked by N-H...Cl, N-H...O, O-H...Cl and O-H...O hydrogen bonds, generating double layers propagating in (100).",

keywords = "conjugation, anti-aromatic, hydrogen bonds, layered structure, crystal structure",

author = "Harrison, {William T. A.} and Plater, {M. John}",

note = "Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the data collection and the EPSRC National Mass Spectrometry Service (University of Swansea) for the HRMS data.",

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AU - Plater, M. John

N1 - Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the data collection and the EPSRC National Mass Spectrometry Service (University of Swansea) for the HRMS data.

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N2 - In the cation of the title hydrated molecular salt, C6H7N2O2+·Cl-·H2O, the six-membered ring shows unequal bond lengths consistent with delocalization of electrons over two separate 6[pi] systems with single bonds between them. In the crystal, the components are linked by N-H...Cl, N-H...O, O-H...Cl and O-H...O hydrogen bonds, generating double layers propagating in (100).

AB - In the cation of the title hydrated molecular salt, C6H7N2O2+·Cl-·H2O, the six-membered ring shows unequal bond lengths consistent with delocalization of electrons over two separate 6[pi] systems with single bonds between them. In the crystal, the components are linked by N-H...Cl, N-H...O, O-H...Cl and O-H...O hydrogen bonds, generating double layers propagating in (100).

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KW - anti-aromatic

KW - hydrogen bonds

KW - layered structure

KW - crystal structure

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