2-Chloro-4-nitrobenzoic acid as a coformer with pharmaceutical cocrystals and molecular salts

2020 ◽  
Vol 76 (8) ◽  
pp. 746-752
Author(s):  
Andreas Lemmerer
Keyword(s):  
Intermolecular Potentials ◽  
Pharmaceutical Cocrystals ◽  
Nitrobenzoic Acid ◽  
Binary Complexes ◽  
Molecular Salts ◽  
Hydrogen Bonded

A series of five binary complexes, i.e. three cocrystals and two molecular salts, using 2-chloro-4-nitrobenzoic acid as a coformer have been produced with five commonly available compounds, some of pharmaceutical relevance, namely, 2-chloro-4-nitrobenzoic acid–isonicotinamide (1/1), C7H4ClNO4·C6H6N2O, 2-chloro-4-nitrobenzoic acid–3,3-diethylpyridine-2,4(1H,3H)-dione (2/1), 2C7H4ClNO4·C9H13NO2, 2-chloro-4-nitrobenzoic acid–pyrrolidin-2-one (1/1), C7H4ClNO4·C4H7NO, 2-carboxypiperidinium 2-chloro-4-nitrobenzoate, C6H12NO2 −·C7H3ClNO4 −, and (2-hydroxyethyl)ammonium 2-chloro-4-nitrobenzoate, C2H8NO+·C7H3ClNO4 −. The coformer falls under the classification of a `generally regarded as safe' compound. All five complexes make use of a number of different heteromeric hydrogen-bonded interactions. Intermolecular potentials were evaluated using the CSD-Materials module.

scholarly journals Role of pK a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids

2021 ◽  
Vol 77 (11) ◽  
Author(s):  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bond ◽  
Shape Index ◽  
Benzoic Acids ◽  
Quinoline Ring ◽  
Nitrobenzoic Acid ◽  
Layer Structures ◽  
Acid And Base ◽  
Short Hydrogen Bond ◽  
Substituted Benzoic Acids ◽  
Hydrogen Bonded

The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4 −, (I), 4-methylquinoline–2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4, (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C10H9.63N0.63+·C7H3.37ClNO4 0.63−, (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C10H9.54N0.54+·C7H3.46ClNO4 0.54−, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4 −, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4 −, have been determined at 185–190 K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O...N distances are 2.5652 (14), 2.556 (3), 2.5485 (13), 2.5364 (13), 2.5568 (13) and 2.5252 (11) Å, respectively, for compounds (I)–(VI). In the hydrogen-bonded acid–base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37 (3):0.63 (3) and 0.46 (3):0.54 (4), respectively, for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)–(VI), π–π stacking interactions between the quinoline ring systems and C—H...O hydrogen bonds are observed. Similar layer structures are constructed in (IV)–(VI) through these interactions together with π–π interactions between the benzene rings of the adjacent acid molecules. A short Cl...Cl contact and an N—O...π interaction are present in (I), while a C—H...Cl hydrogen bond and a π–π interaction between the benzene ring of the acid molecule and the quinoline ring system in (II), and a C—H...π interaction in (III) are observed. Hirshfeld surfaces for the title compounds mapped over d norm and shape index were generated to visualize the weak intermolecular interactions.

scholarly journals Solid-State Versatility of the Molecular Salts/Cocrystals of 2-Chloro-4-nitrobenzoic Acid: A Case Study on Halogen Bonds

ACS Omega ◽  
2017 ◽  
Vol 2 (10) ◽  
pp. 7146-7162 ◽  
Author(s):  
Madhavi Oruganti ◽  
Sunil Kumar Nechipadappu ◽  
Pavan A. Khade ◽  
Darshak R. Trivedi
Keyword(s):  
Solid State ◽  
Halogen Bonds ◽  
Nitrobenzoic Acid ◽  
Molecular Salts

ChemInform Abstract: 2,6-Dimethoxy-3-nitrobenzoic Acid (I). A Hydrogen-Bonded Chain Structure

ChemInform ◽  
2010 ◽  
Vol 22 (26) ◽  
pp. no-no
Author(s):  
G. M. FRANKENBACH ◽  
D. BRITTON ◽  
M. C. ETTER
Keyword(s):  
Chain Structure ◽  
Nitrobenzoic Acid ◽  
Hydrogen Bonded

scholarly journals The Mechanism of Bending in Co-Crystals of Caffeine and 4-Chloro-3-Nitrobenzoic Acid

2021 ◽  
Author(s):  
Amy J. Thompson ◽  
Jason Price ◽  
John McMurtrie ◽  
Jack Clegg
Keyword(s):  
Synchrotron Radiation ◽  
Atomic Resolution ◽  
Mechanical Interlocking ◽  
Elastic Bending ◽  
Nitrobenzoic Acid ◽  
Compression And Expansion ◽  
Hydrogen Bonded

<p>In a recent study, Dey <i>et al.</i><sup>1</sup> propose a mechanism of elastic bending in co-crystals of caffeine, 4-chloro-3-nitrobenzoic acid and methanol (<b>1</b>) in which mechanical interlocking is proposed to allow for the reversible flexibility observed. We have now determined the mechanism to atomic resolution using micro-focused synchrotron radiation,<sup>2</sup> which is different to that previously reported. When subjected to strain the inter-molecular distances change and hydrogen-bonded dimers rotate over two orthogonal directions to allow the compression and expansion producing flexibility. </p>

scholarly journals The Mechanism of Bending in Co-Crystals of Caffeine and 4-Chloro-3-Nitrobenzoic Acid

2021 ◽  
Author(s):  
Amy J. Thompson ◽  
Jason Price ◽  
John McMurtrie ◽  
Jack Clegg
Keyword(s):  
Synchrotron Radiation ◽  
Atomic Resolution ◽  
Mechanical Interlocking ◽  
Elastic Bending ◽  
Nitrobenzoic Acid ◽  
Compression And Expansion ◽  
Hydrogen Bonded

<p>In a recent study, Dey <i>et al.</i><sup>1</sup> propose a mechanism of elastic bending in co-crystals of caffeine, 4-chloro-3-nitrobenzoic acid and methanol (<b>1</b>) in which mechanical interlocking is proposed to allow for the reversible flexibility observed. We have now determined the mechanism to atomic resolution using micro-focused synchrotron radiation,<sup>2</sup> which is different to that previously reported. When subjected to strain the inter-molecular distances change and hydrogen-bonded dimers rotate over two orthogonal directions to allow the compression and expansion producing flexibility. </p>

Can HNNH, FNNH, or HNCHOH bridge the σ-hole and the lone pair at P in binary complexes with H2XP, for X = F, Cl, NC, OH, CN, CCH, CH3, and H?

2015 ◽  
Vol 17 (45) ◽  
pp. 30729-30735 ◽  
Author(s):  
Janet E. Del Bene ◽  
Ibon Alkorta ◽  
José Elguero
Keyword(s):  
Lone Pair ◽  
Binary Complexes ◽  
Bonded Complexes ◽  
Hydrogen Bonded

HNNH and FNNH form either pnicogen-bonded or hydrogen-bonded complexes with H2XP, but only HNCHOH forms both bonds, thereby bridging the σ-hole and the lone pair at P.

scholarly journals Interaction between maleic acid andN-R-furfurylamines: crystal structure of 2-methyl-N-[(5-phenylfuran-2-yl)methyl]propan-2-aminium (2Z)-3-carboxyacrylate andN-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium (2Z)-3-carboxyprop-2-enoate

2017 ◽  
Vol 73 (4) ◽  
pp. 515-519 ◽  
Author(s):  
Elisaveta A. Kvyatkovskaya ◽  
Vladimir P. Zaytsev ◽  
Fedor I. Zubkov ◽  
Pavel V. Dorovatovskii ◽  
Yan V. Zubavichus ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Maleic Acid ◽  
Furan Ring ◽  
Ion Pairs ◽  
Ion Pair ◽  
Cycloaddition Reactions ◽  
Molecular Salts ◽  
Hydrogen Bonded

The title molecular salts, C15H20NO+·C4H3O4−, (I), and C9H15INO+·C4H3O4−, (II), have very similar molecular geometries for both cation and anion. The anions of both (I) and (II) are practically planar (r.m.s. deviations = 0.062 and 0.072 Å, respectively) and adopt a rare symmetrical geometry with the hydroxy H atom approximately equidistant from the two O atoms. In their crystals, the cations and anions in both (I) and (II) form tight ionic pairsviastrong N—H...O hydrogen bonds, with a roughly perpendicular disposition of the anion to the furan ring of the cation. This ion-pair conformation appears to correlate with the lack of reactivity of these salts in [4 + 2] cycloaddition reactions. In the extended structures of (I) and (II), the ion pairs form hydrogen-bonded chains propagating along [010] and [001], respectively,viaN—H...O hydrogen bonds.

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