Five binary supramolecular organic salts constructed from 2-aminoheterocyclic compounds and carboxylic acid derivatives through strong and weak non-covalent interactions

Jin, Shouwen; Zhang, Wenbiao; Liu, Li; Wang, Daqi; He, Hongyong; Shi, Tao; Lin, Feng

doi:10.1016/j.molstruc.2011.01.006

Cited by 34 publications

(3 citation statements)

References 56 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: 90%

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: 90%

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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“…From 292 HM X-ray derived structures in the CSD database, 61 of them present O–H bond distances ranging from 0.71 to 0.88 Å, and at least 24 of them are using the riding model (O–H = 0.82 Å). If we disregard those structures with obvious problems (disorder, twinning, low completeness of the data set, O···O distances greater than 2.50 Å), 16 independent HM anions remain (REFCODE, reference: AFIREO, DIPJER10, FALPEP and TIMOLM01, ISICAP and ISICIX, NUSVUT, OMIGEW - 3 independent HM units, QAYPUC, QUWXEM, RENBAN, VAWPUG, VAZJUD, and YAYYUT). As discussed in the Introduction, the riding model is not useful for compounds with low-barrier hydrogen bonds such as the RAHBs in the HM compound class.…”

Section: Resultsmentioning

confidence: 99%

Predicting the Position of the Hydrogen Atom in the Short Intramolecular Hydrogen Bond of the Hydrogen Maleate Anion from Geometric Correlations

Malaspina

Edwards

Woińska

et al. 2017

Crystal Growth & Design

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The position of the hydrogen atom inside the strong and short intramolecular hydrogen bond of the hydrogen maleate anion strongly varies depending on the crystalline environment. Therefore, it has not been possible in the past to accurately determine it using X-ray diffraction data although there are 292 hydrogen maleate crystal structures with different cations in the literature. In this study, a geometric correlation for the accurate prediction of the hydrogen position in the short intramolecular hydrogen bond is presented. The results used to derive the correlation are obtained from low-temperature neutron-diffraction studies on nine different hydrogen maleate salts that span the whole range from perfectly symmetric to highly asymmetric intramolecular hydrogen bonds. Since the only variable in the correlation as derived from the neutron data is the O•••O distance, the hydrogen atom position in question can subsequently be predicted using information that is accurately available from routine X-ray data. The procedure is tested using high-resolution low-temperature synchrotron X-ray diffraction structures of the same compounds, before it is applied to X-ray data sets found in the literature in which the hydrogen atom position was not determined accurately or not determined at all, e.g., using a riding model.

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“…The application of intermolecular hydrogen bonds is a well-known and efficient tool in the field of organic crystal design because of its strength and directional properties [6][7][8]. Cocrystals and organic salts can be generated through hydrogen bonds [9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Organic Salts Constructed from 6-Hydroxyquinoline and Nitrobenzoic Acids

Ding

Huang

2012

J Chem Crystallogr

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The crystal structures of the proton-transfer salts of 6-hydroxyquinoline with 3,5-dinitrobenzoic acid (1) and 4-nitrobenzoic acid (2) have been determined at room temperature. Their comparative structural features and hydrogen-bonding patterns are described here. Compound 1 crystallizes in the monoclinic P2 1 /c space group, while 2 in the triclinic P-1 space group. Unit cell dimensions and contents are: a = 7.6956 (15), b = 26.075(5), c = 7.7233 (15) Å , b = 95.96(3)°for 1; a = 7.7325(15), b = 8.5939 (17), c = 12.394(3) Å , b = 77.63(3)°for 2. Supramolecular architectures are formed by intermolecular hydrogen bonds in the proton-transfer process. The supramolecular structures are stabilized by N-HÁÁÁO, O-HÁÁÁO and C-HÁÁÁO hydrogen bonds between the two components. Extensive hydrogenbonding interactions give two-dimensional network structures. In addition, p-p stacking interactions exist in the salt 1 due to the aromatic rings.

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Five binary supramolecular organic salts constructed from 2-aminoheterocyclic compounds and carboxylic acid derivatives through strong and weak non-covalent interactions

Cited by 34 publications

References 56 publications

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

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

Predicting the Position of the Hydrogen Atom in the Short Intramolecular Hydrogen Bond of the Hydrogen Maleate Anion from Geometric Correlations

Supramolecular Organic Salts Constructed from 6-Hydroxyquinoline and Nitrobenzoic Acids

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