Hydrogen bonded supramolecular architectures of organic salts based on 5,7-dimethyl-1,8-naphthyridine-2-amine and acidic compounds

Jin, Shouwen; Zhang, Wenbiao; Liu, Li; Gao, Hongfang; Wang, Daqi; Chen, Rongpo; Xu, Xiaoling

doi:10.1016/j.molstruc.2010.04.006

Cited by 46 publications

(4 citation statements)

References 41 publications

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“…3). Similar to our previously published results [33][34][35], in salt 2 the most basic nitrogen atom adjacent to the amine group (for the NH 2 group is a more strong electron-donating group than that of the CH 3 group) in the naphthyridine ring is protonated.…”

Section: Structural Descriptionssupporting

confidence: 91%

Hydrogen Bonded 3D Supramolecular Architectures of Two Organic Salts Constructed from Saccharinate and 2-Aminoheterocyclic Compounds

Jin

Wang

2012

J Chem Crystallogr

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Two saccharinate salts (6-bromobenzo[d]thiazol-2-amine):(saccharin):H 2 O [(HL1) ? Á(sac) -ÁH 2 O, L1 = 6-bromobenzo[d]thiazol-2-amine, (sac) -= saccharinate] (1), and (5,7-dimethyl-1,8-naphthyridine-2-amine):(saccharin) [(HL2) ? Á(sac) -, L2 = 5,7-dimethyl-1,8-naphthyridine-2-amine](2) were prepared and structurally characterized by X-ray crystallography. Salt 1 crystallizes in the triclinic, space group P-1, with a = 7.5523(5) Å , b = 8.6498(7) Å , c = 12.7907(12) Å , a = 99.646(2), b = 90.6500(10)°, c = 97.165(2), V = 816.87(11) Å 3 , Z = 2. Compound 2 crystallizes in the monoclinic, space group P2(1)/c, with a = 8.4237(12) Å , b = 8.0539(11) Å , c = 24.966(2) Å , a = 90°, b = 90.5340(10)°, c = 90°, V = 1693.7(4) Å 3 , Z = 4. The different hydrogen bonding interaction modes of the saccharinate anions and the cations lead to 3D network structure, and 3D ABAB layer structure for 1, and 2, respectively. Despite variations in the aromatic organic bases, there existed strong intermolecular N-HÁÁÁN, and N-HÁÁÁO(carbonyl) hydrogen bonds in both compounds. At the next level, the aromatic C-H proton interacts with the sulfonyl O atom. Compound 1 bears Br-O, and p-p interactions, there are CH 3 -O, and CH-N interactions in 2. These interactions are responsible for the high-yielding supramolecular assembly of 2-aminoheterocyclic compounds and the saccharine into salts.

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Section: Structural Descriptionssupporting

confidence: 91%

Hydrogen Bonded 3D Supramolecular Architectures of Two Organic Salts Constructed from Saccharinate and 2-Aminoheterocyclic Compounds

Jin

Wang

2012

J Chem Crystallogr

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“…5-chloro-2-hydroxybenzaldehyde bears the donor group OH, and may form hydrogen bonds with somecompounds bearing the acceptor groups. We have studied hydrogen bonded assembly of organic acid and organic base [4]. Thedistance d(O1-C1) is 1.217(6) Å, which is typical of C=O bond length, and d(O2-C3) =1.346(6) Åissimilar to the published d(C-O) =1.347 Åreported by Yang [2], but it is longer than the documented data of 1.328(4) Å, which may be contributed to the fact that in our compoud there were stronger hydrogen bonding interactions than in the reported compound [3].The usual intramolecular hydrogen bond is found between the phenol OH group and the carbonyl group to exhibit a S 1 1 6 () graph.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 5-chloro-2-hydroxybenzaldehyde, C7H5ClO2

Jin¹,

Feng²,

Yu³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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C 7 H 5 ClO 2 ,monoclinic, P2 1 (no. 4), a =3.8818(5) Å, b =5.6515(7) Å, c =15. Source of materialCrystals of 5-chloro-2-hydroxybenzaldehyde were formed during an experiment to synthesize an organic acid-base adduct. Asolution of 3,5-dimethylpyrazole (19.2 mg, 0.2 mmol) in 5mL of MeOH was added to aM eOH solution (3 mL) containing 5-chloro-2-hydroxybenzaldehyde (31.3 mg, 0.2 mmol) under continuous stirring. The solution was stirred for about 1ha tr oom temperature, then filtered into atest tube.The filtrate was left at room temperature for several days. Light yellow block-shaped crystals were isolated after slow eva-poration of the solution in air at ambienttemperature.The crystals were collected and dried in air. X-rayd iffraction analysis indicated that no adducts composed of the two components were formed, but crystals of the title compound.

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“…4a, the molecular architecture is very fascinating. Generally, carboxylic acids aggregate in the solid state as dimer, catemer and bridged motifs [57][58][59]. Herein, two carboxyl groups and two inserted water molecules are both bifurcate and construct the R 4 4 ð12Þ rings via O-HÁ Á ÁO hydrogen bonds, which extremely differ from those rings offered by both acidic and basic components together in 1.…”

Section: X-ray Structure Ofmentioning

confidence: 99%