Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5)

The first structure of a strychnine or brucine compound with a zwitterionic species

Graham Smith, Urs D. Wermuth, Peter C. Healy, David J. Young

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The crystal structure of the 1:1 adduct hydrate of strychnine with 1,7-Cleve's acid (8-amino-2-naphthalenesulfonic acid), namely strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5) has been determined and provides a unique example of a neutral association involving strychnine and an achiral zwitterionic acid species, previously unobserved in the structures of either strychnine or brucine addition compounds. Crystals are orthorhombic, space group P212121, with Z=4 in a cell with dimensions a=10.4484(8), b=30.850(3), c=9.4998(11) Å. Hydrogen bonding involving all available proton-donor and acceptor sites on all species gives rise to a three-dimensional framework polymer structure. The crystallographic literature for strychnine and brucine and their compounds is also reviewed.

Original languageEnglish
Pages (from-to)805-811
Number of pages7
JournalJournal of Chemical Crystallography
Volume36
Issue number12
DOIs
Publication statusPublished - Dec 2006
Externally publishedYes

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strychnine
Strychnine
Water
water
acids
Hydrogen Bonding
Hydrates
hydrates
adducts
Protons
Hydrogen bonds
Polymers
Crystal structure
2-naphthalenesulfonic acid
brucine
Association reactions
Crystals
crystal structure
Acids
protons

Cite this

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title = "Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5): The first structure of a strychnine or brucine compound with a zwitterionic species",
abstract = "The crystal structure of the 1:1 adduct hydrate of strychnine with 1,7-Cleve's acid (8-amino-2-naphthalenesulfonic acid), namely strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5) has been determined and provides a unique example of a neutral association involving strychnine and an achiral zwitterionic acid species, previously unobserved in the structures of either strychnine or brucine addition compounds. Crystals are orthorhombic, space group P212121, with Z=4 in a cell with dimensions a=10.4484(8), b=30.850(3), c=9.4998(11) {\AA}. Hydrogen bonding involving all available proton-donor and acceptor sites on all species gives rise to a three-dimensional framework polymer structure. The crystallographic literature for strychnine and brucine and their compounds is also reviewed.",
keywords = "1,7-Cleve's acid, Hydrogen bonding, Molecular adduct, Naphthylaminesulfonic acids, Strychnine",
author = "Graham Smith and Wermuth, {Urs D.} and Healy, {Peter C.} and Young, {David J.}",
year = "2006",
month = "12",
doi = "10.1007/s10870-006-9085-5",
language = "English",
volume = "36",
pages = "805--811",
journal = "Journal of Chemical Crystallography",
issn = "1074-1542",
publisher = "Springer New York",
number = "12",

}

Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5) : The first structure of a strychnine or brucine compound with a zwitterionic species. / Smith, Graham; Wermuth, Urs D.; Healy, Peter C.; Young, David J.

In: Journal of Chemical Crystallography, Vol. 36, No. 12, 12.2006, p. 805-811.

Research output: Contribution to journalArticleResearchpeer-review

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T2 - The first structure of a strychnine or brucine compound with a zwitterionic species

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AU - Wermuth, Urs D.

AU - Healy, Peter C.

AU - Young, David J.

PY - 2006/12

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AB - The crystal structure of the 1:1 adduct hydrate of strychnine with 1,7-Cleve's acid (8-amino-2-naphthalenesulfonic acid), namely strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5) has been determined and provides a unique example of a neutral association involving strychnine and an achiral zwitterionic acid species, previously unobserved in the structures of either strychnine or brucine addition compounds. Crystals are orthorhombic, space group P212121, with Z=4 in a cell with dimensions a=10.4484(8), b=30.850(3), c=9.4998(11) Å. Hydrogen bonding involving all available proton-donor and acceptor sites on all species gives rise to a three-dimensional framework polymer structure. The crystallographic literature for strychnine and brucine and their compounds is also reviewed.

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KW - Molecular adduct

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