scholarly journals Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid

2022 ◽  
Vol 78 (1) ◽  
Author(s):  
Jan Henrik Halz ◽  
Andreas Hentsch ◽  
Christoph Wagner ◽  
Kurt Merzweiler
Keyword(s):  
Hydrogen Bonding ◽  
Nitrogen Atom ◽  
Crystal Structures ◽  
Schiff Bases ◽  
Molecular Fragment ◽  
Supramolecular Structures ◽  
Hydrogen Bridge ◽  
Aminobenzoic Acid ◽  
Aminobenzoic Acids ◽  
Hydrogen Bonding Networks

Treatment of 3-formylacetylacetone with the isomeric o-, m- and p-aminobenzoic acids led to the formation of the corresponding Schiff bases, namely, 3-[(2-carboxyphenylamino)methylidene]pentane-2,4-dione, 1, 3-[(3-carboxyphenylamino)methylidene]pentane-2,4-dione, 2, and 3-[(4-carboxyphenylamino)methylidene]pentane-2,4-dione, 3, all C13H13NO4, that contain a planar amino-methylene-pentane-2,4-dione core with a strong intramolecular N—H...O hydrogen bridge. The carboxyphenyl groups attached to the nitrogen atom are almost coplanar to the central molecular fragment. Depending on the position of the carboxyl unit, different supramolecular structures with hydrogen-bonding networks are formed in the three title structures.

Molecular Cocrystals of Carboxylic Acids. XXVI Adducts of the Amino-Substituted Benzoic Acids with Nitroaromatic Lewis Bases: the Influence of Associative Polyfunctional Substituents on Self-Assembly of Molecules in Cocrystallization Processes

1997 ◽  
Vol 50 (10) ◽  
pp. 977 ◽  
Author(s):  
Daniel E. Lynch ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectroscopy ◽  
Self Assembly ◽  
Benzoic Acids ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Lewis Bases ◽  
Aminobenzoic Acids ◽  
Substituted Benzoic Acids

A series of molecular adducts of the isomeric aminobenzoic acids with the nitro-substituted Lewis bases 2-chloro-5-nitropyridine, 5-nitroquinoline and 5-nitroisoquinoline has been prepared and characterized by using infrared spectroscopy and X-ray powder diffraction, and in four cases by single-crystal X-ray diffraction methods. These four compounds are the adducts of 3-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)(C9H6N2O2)], 4-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)2(C9H6N2O2)], 2-aminobenzoic acid with 5-nitroisoquinoline [(C7H7NO2)(C9H6N2O2)] and 4-aminobenzoic acid with 5-nitroisoquinoline [(C7H7N2O2)(C9H6N2O2)]. Other compounds described are the (1 : 1) adducts of 4-aminobenzoic acid with 2-chloro-5-nitropyridine, and 2-aminobenzoic acid with 5-nitroquinoline. All adducts involve hydrogen-bonding network associations while in none of the examples is any proton transfer involved.

The crystalline forms of nine hydrochloride salts of substituted tryptamines

2021 ◽  
Vol 77 (10) ◽  
pp. 615-620
Author(s):  
Duyen N. K. Pham ◽  
Zachary S. Belanger ◽  
Andrew R. Chadeayne ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Two Dimensional ◽  
One Dimensional ◽  
Hydrogen Bonding Networks ◽  
Hydrogen Bonding Network ◽  
Crystalline Forms

The crystal structures of the hydrochloride salts of nine substituted tryptamines, namely, 1-methyltryptammonium chloride, C11H15N2 +·Cl−, (1), 2-methyl-1-phenyltryptammonium chloride, C17H19N2 +·Cl−, (2), 5-methoxytryptammonium chloride, C11H15N2O+·Cl−, (3), 5-bromotryptammonium chloride, C10H12BrN2 +·Cl−, (4), 5-chlorotryptammonium chloride, C10H12ClN2 +·Cl−, (5), 5-fluorotryptammonium chloride, C10H12FN2 +·Cl−, (6), 5-methyltryptammonium chloride, C11H15N2 +·Cl−, (7), 6-fluorotryptammonium chloride, C10H12FN2 +·Cl−, (8), and 7-methyltryptammonium chloride, C11H15N2 +·Cl−, (9), are reported. The seven tryptamines with N—H indoles, (3)–(9), show very similar structures, with N—H...Cl hydrogen-bonding networks forming two-dimensional sheets in the crystals. These sheets are combinations of R 4 2(8) and R 4 2(18) rings, and C 2 1(4) and C 2 1(9) chains. Substitution at the indole N atom reduces the dimensionality of the hydrogen-bonding network, with compounds (1) and (2) demonstrating one-dimensional chains that are a combination of different rings and parallel chains.

scholarly journals Hydrogen-bonding in mono-, di- and tetramethylammonium dihydrogenphosphites

2021 ◽  
Vol 236 (1-2) ◽  
pp. 33-41
Author(s):  
Matthias Kogler ◽  
Berthold Stöger
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
High Temperature ◽  
Low Temperature ◽  
Crystal Structures ◽  
Point Symmetry ◽  
Temperature Dependent ◽  
Threefold Axis ◽  
Quotient Graphs ◽  
Hydrogen Bonding Networks

Abstract The crystal structures of methylammonium and dimethylammonium dihydrogenphosphite (MA⋅H2PO3, I2/a and DMA⋅H2PO3, P 2 1 / c $P{2}_{1}/c$ ) are built of infinite chains of hydrogen bonded H 2 P O 3 − ${\mathrm{H}}_{\mathrm{2}}\mathrm{P}{\mathrm{O}}_{\mathrm{3}}^{-}$ anions. The chains are connected by the ammonium cations via hydrogen bonding to di- (DMA⋅H2PO3) and triperiodic (MA⋅H2PO3) networks. Tetramethylammonium dihydrogenphosphite monohydrate (TMA⋅H2PO3⋅H2O) features temperature dependent dimorphism. The crystal structure of the high-temperature (HT, cubic P213) and low-temperature (LT, orthorhombic P212121) phases were determined at 150 and 100 K, respectively. The hydrogen bonding network in the HT phase is disordered, with H 2 P O 3 − ${\mathrm{H}}_{\mathrm{2}}\mathrm{P}{\mathrm{O}}_{\mathrm{3}}^{-}$ and H2O being located on a threefold axis and is ordered in the LT phase. On cooling, the point symmetry is reduced by an index of 3. The lost symmetry is retained as twin operations, leading to threefold twinning by pseudo-merohedry. The hydrogen-bonding networks of the HT and LT phases can be represented by undirected and directed quotient graphs, respectively.

scholarly journals Crystal structures of two erbium(III) complexes with 4-aminobenzoic acid and 4-chloro-3-nitrobenzoic acid

2015 ◽  
Vol 71 (12) ◽  
pp. 1457-1461 ◽  
Author(s):  
Graham Smith ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Bond Length ◽  
Dimethyl Sulfoxide ◽  
Crystal Structures ◽  
Water Molecules ◽  
Aminobenzoic Acid ◽  
Coordination Polyhedra ◽  
Nitrobenzoic Acid ◽  
The Third ◽  
Length Range

The crystal structures of two erbium(III) complexes with 4-aminobenzoic acid (4-ABAH), namely bis(μ2-4-aminobenzoato-κ2O:O′)bis[bis(4-aminobenzoato-κ2O,O′)diaquaerbium(III)] dihydrate, [Er2(C7H6NO2)6(H2O)4]·2H2O, (I), and 4-chloro-3-nitrobenzoic acid (CLNBAH), namely poly[hexakis(μ2-4-chloro-3-nitrobenzoato-κ2O:O′)bis(dimethyl sulfoxide-κO)dierbium(III)], [Er2(C7H3ClNO4)6(C2H6OS)2]n, (II), have been determined. In the structure of solvatomorphic compound (I), the symmetry-related irregular ErO8coordination polyhedra in the discrete centrosymmetric dinuclear complex comprise two monodentate water molecules and six carboxylate O-atom donors, four from two bidentate carboxylateO,O′-chelate groups and two from the bis-monodentateO:O′-bridging group of the third 4-ABA anion. The Er—O bond-length range is 2.232 (3)–2.478 (3) Å and the Er...Er separation in the dinuclear complex unit is 4.7527 (4) Å. One of the coordinating water molecules is involved in an intra-unit O—H...O hydrogen-bonding association with an inversion-related carboxylate O-atom acceptor. In contrast, the anhydrous compound (II) is polymeric, based on centrosymmetric dinuclear repeat units comprising ErO7coordination polyhedra which involve four O-atom donors from two bidentateO:O′-bridging carboxylate groups, one O-atom donor from the monodentate dimethyl sulfoxide ligand and two O-atom donors from the third bridging CLNBA anion. The latter provides the inter-unit link in the one-dimensional coordination polymer extending along [100]. The Er—O bond-length range in (II) is 2.239 (6)–2.348 (6) Å and the Er...Er separation within the dinuclear unit is 4.4620 (6) Å. In the crystal of (I), extensive inter-dimer O—H...O and N—H...O hydrogen-bonding interactions involving both the coordinating water molecules and the solvent water molecules, as well as the amine groups of the 4-ABA anions, give an overall three-dimensional network structure. Within this structure are also weak π–π ring interactions between two of the coordinating ligands [ring-centroid separations = 3.676 (3) and 3.711 (2) Å]. With (II), only weak intra-polymer C—H...O, C—H...Cl and C—H...S interactions are present.

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