2008
DOI: 10.1107/s1600536808024616
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2,2′-Dimethyl-7,7′-(methylenediimino)di-1,8-naphthyridin-1-ium bis(perchlorate)

Abstract: Key indicators: single-crystal X-ray study; T = 113 K; mean (C-C) = 0.005 Å; disorder in solvent or counterion; R factor = 0.060; wR factor = 0.134; data-toparameter ratio = 12.6.In the title salt, C 19 H 20 N 6 2+ Á2ClO 4 À , the two planar 1,8-naphthyridine systems are linked by a methylenediamine group with a dihedral angle of 60.6 (1) between the two systems. The crystal structure involves extensive N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonding. Related literature Data collectionBruker SMART CCD area-detecto… Show more

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Cited by 6 publications
(3 citation statements)
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“…This is a salt where the OH groups of 2,4,6-trinitrophenol are ionized by proton transfer to one nitrogen atom (N(2)) of the naphthyridine moieties, which is also confirmed by the bond distance of O(1)AC(11) (1.256(3) Å) for phenolate (1.24 ± 0.01 Å) [24]. In this case the less basic nitrogen atom close to the methyl group is protonated which is similar to the published result [25], but it is different from the compound 1. In the compound, there is one ion pair without solvent molecules, which is well agreement with the micro-analysis results.…”
Section: Preparation and General Characterizationsupporting
confidence: 87%
“…This is a salt where the OH groups of 2,4,6-trinitrophenol are ionized by proton transfer to one nitrogen atom (N(2)) of the naphthyridine moieties, which is also confirmed by the bond distance of O(1)AC(11) (1.256(3) Å) for phenolate (1.24 ± 0.01 Å) [24]. In this case the less basic nitrogen atom close to the methyl group is protonated which is similar to the published result [25], but it is different from the compound 1. In the compound, there is one ion pair without solvent molecules, which is well agreement with the micro-analysis results.…”
Section: Preparation and General Characterizationsupporting
confidence: 87%
“…5. In this case the less basic nitrogen atom close to the methyl group is protonated which is similar to the published result [31], but it is different from the compounds 1 and 2. There exist two NAHÁÁÁO hydrogen bonds between the oxygen atom of the carboxylate and the amine group (1) interaction, which is similar to the monoanion of maleic acid in forming intramolecular hydrogen bonds [32].…”
Section: Structural Descriptionssupporting
confidence: 84%
“…with the NH þ on the naphthyridine rings in 2 resembles 2-amino-4,6-dimethylpyridinium cations [28]. Similar to the organic salt 2,2 0 -dimethyl-7,7 0 (methylenediimino)di-1,8-naphthyridin-1-ium bis(perchlorate) [29], the less basic ring N has been protonated. The coordination geometry around Cd(II) is a distorted tetrahedron with four chlorides.…”
Section: Structural Descriptionsmentioning
confidence: 94%