Molecular structure, interatomic interactions and vibrational analysis of 1,4-diazabicyclo[3.2.1]octane parent ring system

7-Azabicyclo[2.2.1]heptane (7-azanorbornane) is a bridged heterocyclic nucleus found in epibatidine, the alkaloid isolated from the skin of the tropical poison frog Epipedobates tricolor. Since epibatidine is known as one of the most potent acetylcholine nicotinic receptor agonists, a plethora of literature has been devoted to this alkaloid. However, there are no structural data on the unsubstituted 7-azanorbornane, the parent bicyclic ring of epibatidine and its derivatives. We herein present the structural characterization of the 7-azabicyclo[2.2.1]heptane parent ring as its hydrochloride salt, namely 7-azabicyclo[2.2.1]heptan-7-ium chloride, C 6 H 12 N + ÁCl À . The compete cation is generated by a crystallographic mirror plane with the N atom lying on the mirror, as does the chloride anion. In the crystal, the cations are linked to the anions by N-HÁ Á ÁCl hydrogen bonds, which generate [001] chains.

show abstract

The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride

Britvin

Rumyantsev

2017

Acta Cryst E

Self Cite

View full text Add to dashboard Cite

show abstract

Crystal structure of (1R,5S)-endo-(8-methyl-8-azoniabicyclo[3.2.1]oct-3-yl)ammonium aquatrichloridonitratocopper(II)

Britvin

Rumyantsev

2017

Acta Cryst E

Self Cite

View full text Add to dashboard Cite

The structure of a salt of diprotonated endo-3-aminotropane crystallized with a copper(II) anionic cluster is reported, viz.Neither ion in the salt has been structurally characterized previously. In the crystal, the ions pack together to form a three-dimensional structure held together by a network of intermolecular N-HÁ Á ÁO, O-HÁ Á ÁCl and N-HÁ Á ÁCl hydrogen-bonding interactions. Selective crystallization of the title compound can be considered as a simple method for the separation of the exo and endo isomers of 3-aminotropane.

show abstract

Crystal structure of (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide

Britvin

Rumyantsev

2017

Acta Cryst E

Self Cite

View full text Add to dashboard Cite

The cage of 2,5-diazabicyclo[2.2.1]heptane is frequently employed in synthetic chemistry as a rigid bicyclic counterpart of the piperazine ring. The 2,5-diazabicyclo[2.2.1]heptane scaffold is incorporated into a variety of compounds having pharmacological and catalytic applications. The unsubstituted parent ring of the system, 2,5-diazabicyclo[2.2.1]heptane itself, has not been structurally characterized. We herein report on the molecular structure of the parent ring in (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide, C 5 H 12 N 2 2+ Á2Br À . The asymmetric unit contains two crystallographically independent cages of 2,5-diazabicyclo[2.2.1]heptane. Each cage is protonated at the two nitrogen sites. The overall charge balance is maintained by four crystallographically independent bromide ions. In the crystal, the components of the structure are linked via a complex three-dimensional network of N-HÁ Á ÁBr hydrogen bonds.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Molecular structure, interatomic interactions and vibrational analysis of 1,4-diazabicyclo[3.2.1]octane parent ring system

Cited by 3 publications

References 49 publications

The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride

The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride

Crystal structure of (1R,5S)-endo-(8-methyl-8-azoniabicyclo[3.2.1]oct-3-yl)ammonium aquatrichloridonitratocopper(II)

Crystal structure of (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide

Contact Info

Product

Resources

About