Quaternary Cocrystals of 3,5-Dihydroxybenzoic Acid

Rajkumar Madhu

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Quaternary Cocrystals of 3,5-Dihydroxybenzoic Acid

机译：3,5-二羟基苯甲酸的季酸盐

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One-pot synthesis of a series of four quaternary cocrystals of 3,5-dihydroxybenzoic (DHB) acid is outlined strategically based on the long-range synthon Aufbau modules (LSAM) approach exploiting hierarchical hydrogen bonding interactions. In these quaternary cocrystals, heteromeric O-H-(phenolic)center dot center dot center dot N-(pyridine) hydrogen bonds form a discrete closed synthon and additional heteromeric O-H-(carboxylic)center dot center dot center dot N-(pyridine) hydrogen bonds which lead to the formation of a one-dimensional structure. Of four quaternary cocrystals isolated, two pseudopolymorphs of DHB with tetramethylpyrazine (TMP), phenazine (PHE), and pyrene (PYR) (2:1:2:1 and 2:2:1:2 stoichiometric ratio) are observed. Both these pseudopolymorphs are composed of closed 0D tetrameric synthons consisting of two identical and distinct linker bases. Among these two, the quaternary cocrystals with stoichiometry of 2:1:2:1 are linked through DHB and PHE forming a symmetrical closed tetramer synthon, whereas quaternary cocrystals with 2:2:1:2 stoichiometric ratio are connected through DHB, TMP, and PHE forming an unsymmetrical closed tetramer synthon (anomalous synthon).

机译：基于利用层次氢键相互作用的长程synthon-Aufbau模块（LSAM）方法，从战略上概述了3,5-二羟基苯甲酸（DHB）系列四个四元共晶体的一锅法合成。在这些四元共晶体中，异聚O-H-（酚）中心点N-（吡啶）氢键形成离散的闭合合成子和额外的异聚O-H-（羧基）中心点N-（吡啶）氢键，从而形成一维结构。在分离的四个四元共晶体中，观察到了DHB与川芎嗪（TMP）、吩嗪（PHE）和芘（PYR）（2:1:2:1和2:2:1:2化学计量比）的两个假多晶型。这两种假多晶型都由封闭的0D四聚体合成子组成，由两个相同且不同的连接基组成。其中，化学计量比为2:1:2:1的四元共晶通过DHB和PHE连接，形成对称的封闭四聚体合成子，而化学计量比为2:2:1:2的四元共晶通过DHB、TMP和PHE连接，形成不对称的封闭四聚体合成子（反常合成子）。

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《Crystal growth & design》 |2021年第6期|共7页
作者
Rajkumar Madhu;
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Indian Inst Sci Solid State &

Struct Chem Unit Bangalore 560012 Karnataka India;

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正文语种 eng
中图分类晶体学;
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1. Modification of the supramolecular hydrogen-bonding patterns of acetazolamide in the presence of different cocrystal formers: 3:1, 2:1, 1:1, and 1:2 cocrystals from screening with the structural isomers of hydroxybenzoic acids, aminobenzoic acids, hydroxybenzamides, aminobenzamides, nicotinic acids, nicotinamides, and 2,3-dihydroxybenzoic acids [J] . Arenas-García J.I., Herrera-Ruiz D., Mondragón-Vásquez K., Crystal growth & design . 2012,第2期

机译：通过与羟基苯甲酸，氨基苯甲酸，羟基苯甲酰胺的结构异构体筛选得到的不同共晶形成剂：3：1、2：1、1：1和1：2共晶存在下，对乙酰唑胺的超分子氢键模式进行修饰氨基苯甲酰胺，烟酸，烟酰胺和2,3-二羟基苯甲酸
2. Binary polymorphic cocrystals: an update on the available literature in the Cambridge Structural Database, including a new polymorph of the pharmaceutical 1:1 cocrystal theophylline–3,4‐dihydroxybenzoic acid [J] . Mnguni Malitsatsi J., Michael Joseph P., Lemmerer Andreas Acta crystallographica. Section C, Structural chemistry. . 2018,第6期

机译：二元多态性cocrystals：剑桥结构数据库中可用文献的更新，包括药物的新多晶型物1：1个Cocrystal茶碱-3,4-二羟基苯甲酸
3. Intramolecular [2+2] photocycloaddition of bichromophoric derivatives of 3,5-dihydroxybenzoic acid and 3,5-dihydroxybenzonitrile [J] . Hoffmann N., Pete JP. Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2001,第8Speca期

机译：3,5-二羟基苯甲酸和3,5-二羟基苄腈的双色衍生物的分子内[2 + 2]光环加成
4. In situ investigation of Parazinamide-2,5-dihydroxybenzoic acid cocrystal formed via slurry crystallization [C] . Hao Jing, Xie chuang International Forum on Crystal Engineering and Smart Manufacturing;Tianjin University;Tianjin Science and Technology Association . -1

机译：以浆料结晶形成的悖论酰胺-2,5-二羟基苯甲酸烯酮的原位研究
5. Kinetic studies of the hydrolysis of 3,5-diketo acids by fumarylacetoacetate fumarylhydrolase. [D] . Angus, Ronald H. 1976

机译：富马酰乙酰乙酸富马酰水解酶水解3,5-二酮酸的动力学研究。
6. Quaternary cocrystals: combinatorial synthetic strategies based on long-range synthon Aufbau modules (LSAM) [O] . Ritesh Dubey, Niyaz A. Mir, Gautam R. Desiraju 2016

机译：第四元共晶体：基于远程合成子Aufbau模块（LSAM）的组合合成策略
7. Different acid-base behaviour of a pyrazole and an isoxazole with organic acids: crystal and molecular structures of the salt 3-(4-fluorophenyl)-1H-pyrazolium 2,4,6-trinitrophenolate and of the cocrystal 4-amino-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide-3,5-dinitrobenzoic acid (1/1) [O] . Girisha M., Yathirajan H. S., Jasinski Jerry P., 2016

机译：吡唑和异恶唑与有机酸的不同酸碱行为：3-（4-氟苯基）-1H-吡唑鎓2,4,6-三硝基苯酚盐和共结晶4-氨基-N-盐的晶体和分子结构（3,4-二甲基-1,2-恶唑-5-基）苯磺酰胺-3,5-二硝基苯甲酸（1/1）
8. Analyzing carboxylic acid and amine-nitro hydrogen-bond geometry in the cocrystal of 4-aminobenzoic acid and 3,5-dinitrobenzoic acid by use of 298 K X-ray and 15 K neutron diffraction. [R] . Frankenbach, G. M., Etter, M. C., Schultz, A. J., 1993

机译：通过使用298K X射线和15K中子衍射分析4-氨基苯甲酸和3,5-二硝基苯甲酸的共晶中的羧酸和胺 - 硝基氢键几何结构。

Quaternary Cocrystals of 3,5-Dihydroxybenzoic Acid

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