The complexation of 2,4-dinitrophenol with basic drugs

Acid + base = salt

M. John Plater (Corresponding Author), William T. A. Harrison

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Abstract

Different drugs containing a basic nitrogen atom were crystallised with 2,4-dinitrophenol to study the mode of complexation in search of an antidote to 2,4-dinitrophenol poisoning. The protonated forms of quininium, quinidinium and trazodonium form N–H···O hydrogen bonds to the deprotonated O atom of the 2,4-dinitrophenolate anion, whereas haloperidolium forms a bifurcated N–H···(O,O) hydrogen bond to the deprotonated O atom of 2,4-dinitrophenol and an O atom of the adjacent nitro group. Hydrogen-bonded chains occur in the quininium, quinidinium and haloperidolium crystal structures, whereas the trazodonium structure consists of ion pairs. These results are discussed with a view to lowering the toxicity of 2,4-dinitrophenol in the body in the case of an overdose.
Original languageEnglish
Pages (from-to)281-286
Number of pages6
JournalJournal of Chemical Research
Volume48
Issue number7-8
Early online date17 Jul 2019
DOIs
Publication statusPublished - Jul 2019

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2,4-Dinitrophenol
Complexation
Salts
Atoms
Acids
Pharmaceutical Preparations
Hydrogen bonds
Antidotes
Anions
Toxicity
Hydrogen
Nitrogen
Crystal structure
Ions
quinidinium

Keywords

  • 2,4-dinitrophenol
  • haloperidolium
  • quinidinium
  • quininium
  • trazodonium
  • DINITROPHENOL

Cite this

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title = "The complexation of 2,4-dinitrophenol with basic drugs: Acid + base = salt",
abstract = "Different drugs containing a basic nitrogen atom were crystallised with 2,4-dinitrophenol to study the mode of complexation in search of an antidote to 2,4-dinitrophenol poisoning. The protonated forms of quininium, quinidinium and trazodonium form N–H···O hydrogen bonds to the deprotonated O atom of the 2,4-dinitrophenolate anion, whereas haloperidolium forms a bifurcated N–H···(O,O) hydrogen bond to the deprotonated O atom of 2,4-dinitrophenol and an O atom of the adjacent nitro group. Hydrogen-bonded chains occur in the quininium, quinidinium and haloperidolium crystal structures, whereas the trazodonium structure consists of ion pairs. These results are discussed with a view to lowering the toxicity of 2,4-dinitrophenol in the body in the case of an overdose.",
keywords = "2,4-dinitrophenol, haloperidolium, quinidinium, quininium, trazodonium, DINITROPHENOL",
author = "Plater, {M. John} and Harrison, {William T. A.}",
note = "Acknowledgements We thank the National Mass Spectrometry Service Centre (University of Swansea) for mass spectrometry data and the UK National Crystallographic Service (University of Southampton) for intensity data collections. Funding The author(s) received no financial support for the research, authorship and/or publication of this article.",
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language = "English",
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N1 - Acknowledgements We thank the National Mass Spectrometry Service Centre (University of Swansea) for mass spectrometry data and the UK National Crystallographic Service (University of Southampton) for intensity data collections. Funding The author(s) received no financial support for the research, authorship and/or publication of this article.

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N2 - Different drugs containing a basic nitrogen atom were crystallised with 2,4-dinitrophenol to study the mode of complexation in search of an antidote to 2,4-dinitrophenol poisoning. The protonated forms of quininium, quinidinium and trazodonium form N–H···O hydrogen bonds to the deprotonated O atom of the 2,4-dinitrophenolate anion, whereas haloperidolium forms a bifurcated N–H···(O,O) hydrogen bond to the deprotonated O atom of 2,4-dinitrophenol and an O atom of the adjacent nitro group. Hydrogen-bonded chains occur in the quininium, quinidinium and haloperidolium crystal structures, whereas the trazodonium structure consists of ion pairs. These results are discussed with a view to lowering the toxicity of 2,4-dinitrophenol in the body in the case of an overdose.

AB - Different drugs containing a basic nitrogen atom were crystallised with 2,4-dinitrophenol to study the mode of complexation in search of an antidote to 2,4-dinitrophenol poisoning. The protonated forms of quininium, quinidinium and trazodonium form N–H···O hydrogen bonds to the deprotonated O atom of the 2,4-dinitrophenolate anion, whereas haloperidolium forms a bifurcated N–H···(O,O) hydrogen bond to the deprotonated O atom of 2,4-dinitrophenol and an O atom of the adjacent nitro group. Hydrogen-bonded chains occur in the quininium, quinidinium and haloperidolium crystal structures, whereas the trazodonium structure consists of ion pairs. These results are discussed with a view to lowering the toxicity of 2,4-dinitrophenol in the body in the case of an overdose.

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