4-dimethylaminopyridine Research Articles

A Convenient Green Protocol for the Synthesis of 4-Arylmethylidene-3-substituted-isoxazol-5(4H)-ones catalysed by Dimethylaminopyridine (DMAP)

Isoxazolemotif containing heterocyclic compounds are important for their wide range of biological activities. Therefore, in the present article, I report a convenient and green protocol for the synthesis of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-ones by the one pot three component reaction of aldehydes, β-keto ester and hydroxylamine hydrochloride catalyzed by Dimethylaminopyridine (DMAP). 1 (a-i) 2(a-b) 3 (4a-f), (5a-i) Scheme 1: Reagent and conditions:(i) Dimethylaminopyridine (DMAP), H2O (5 mL), 70- 800C, 6 to 25 min.

Brightly Luminescent Platinum Complexes of N∧C-∧N Ligands Forming Six-Membered Chelate Rings: Offsetting Deleterious Ring Size Effects Using Site-Selective Benzannulation.

Brightly emissive platinum(II) complexes (λemission,max = 607-612 nm) of the type RLPtCl are reported, where RL is a cyclometalated N∧C-∧N-coordinating ligand derived from 1,3-di(2-trifluoromethyl-4-phenanthridinyl)benzene (CF3LH) or 1,3-di(2-tert-butyl-4-phenanthridinyl)benzene (tBuLH). Metathesis of the chlorido ligand can be achieved under mild conditions, enabling isolation of ionic compounds with the formula [CF3LPtL']PF6 where L' = pyridine or (4-dimethylamino)pyridine (DMAP), as well as the charge-neutral species tBuLPt(C≡C─C6H4─tBu) (C≡C─C6H4─tBu = 4-tert-butylphenylacetylido). Compared with N∧N∧N-ligated Pt(II) complexes that form 5-membered chelates, these compounds all contain 6-membered rings. Expanding the chelate ring size from 5 to 6 has been previously demonstrated to enhance emission in some N∧N∧N-coordinated Pt(II) species─for example, in complexes of 2,6-di(8-quinolinyl)pyridine vs those of 2,2':6',2″-terpyridine─but in related N∧C-∧N-coordinated species, luminescence quantum yields are significantly lower for the 6-membered chelate ring complexes. Here, we demonstrate that site-selective benzannulation of the quinolinyl side-arms can offset the deleterious effect of changing the chelate ring-size and boost photophysical properties such as the quantum yield. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations suggest that benzannulation counterintuitively destabilizes the emissive triplet states compared to the smaller π-system, with the "imine-bridged biphenyl" form of the phenanthridinyl arm helping to buffer against larger molecular distortions, enhancing photoluminescence quantum yields up to 0.09 ± 0.02. The spontaneous formation under aerated conditions of a Pt(IV) derivative (CF3LPtCl3) is also reported, together with its molecular structure in the solid state.

4-(Dimethylamino)pyridine as an Efficient Catalyst for One-Pot Synthesis of 1,4-Pyranonaphthoquinone Derivatives viaMicrowave-Assisted Sequential Three Component Reaction in Green Solvent

Novel 1,4-pyranonaphthoquinone derivatives were successfully synthesized via the microwave-assisted three-component reaction of 1,4-naphthoquinone, malononitrile, and various arylaldehydes in ethanol in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst, and subsequently evaluated in terms of their antimicrobial and antifungal activities. This synthetic procedure has the notable advantages of environmental friendliness, short reaction time, good yield, and convenient operation.

Synthesis of isoeugenol biobased epoxy polymer by forming α‐hydroxyl ester and degradation studies

AbstractThe synthesis of bio‐based monomers and polymers from renewable feedstock, such as plant biomass, is desirable because of the depletion of fossil fuel resources and the reliance of thermosetting epoxy resin on non‐renewable petrochemical monomers. Despite the excellent polymeric properties of bisphenol‐based epoxy resins, these negatively impact human health. Herein, the synthesis of self‐curable epoxy polymers from the bio‐based material isoeugenol by forming α‐hydroxyl esters is reported. The epoxides are named AB (single epoxide and ester groups) and A2B2 (double epoxide and ester groups), based on the number of active ester and epoxide groups. The materials derived from the bio‐based material, AB and A2B2, were initiated with and without the catalyst N,N′‐dimethylaminopyridine (DMAP) and curing agent diaminodiphenylmethane. Without the catalyst, AB and A2B2 self‐polymerized at 247 and 210°C, respectively. Notably, the polymerization temperatures for AB and A2B2 decreased after the addition of DMAP. The self‐cured epoxy resin without the catalyst showed the highest thermal stability and glass transition temperature (Tg = 156°C). Degradation and recovery studies suggested forward that 51% of the material could be recovered and 94% of the polymer could be degraded from the self‐cured A2B2 in 25 wt% NaOH solution.

Design, Synthesis of a Novel Banana-Shaped Compounds via Esterification

Schiff's Bases were synthesized from the reaction of p-amino benzoic acid and alkoxybenzaldehyde in absolute ethanol and reacted with (E)-3-((4-hydroxybenzylidene) amino) phenol used DCC (N,N'-Dicyclocarbodiimide) and DAMP (4-(Dimethylamino) pyridine ) to 3-(((E)-4-((4-(((E)-4 alkoxy benzylidene) amino) benzoyl) oxy) benzylidene) amino) phenyl4- (E)- 4-alkoxy benzyli dene ) amino) benzoate. The structures of the products were confirmed by their melting points, FT-IR, 1HNMR spectra.

Conjugation of 4-(dimethylamino)pyridine to primary amines in aqueous buffer solutions using an N-hydroxysuccinimide ester reagent

An N-hydroxysuccinimide (NHS) ester reagent bearing an N-protonated 4-(dimethylamino)pyridine (DMAP) moiety was synthesized as a stable solid. N-Protonation temporarily deactivated the nucleophilic pyridine nitrogen, to induce compatibility with the NHS ester moiety. Using this reagent, DMAP was conjugated to primary amines in aqueous buffer solutions in high yield.

Stereoretention in the Bulk ROP of l-Lactide Guided by a Thermally Stable Organocatalyst.

Polylactide (PLA) has emerged as one of the most promising bio-based alternatives to petroleum-based plastics, mainly because it can be produced from the fermentation of naturally occurring sugars and because it can be industrially compostable. In spite of these benefits, the industrial ring-opening polymerization (ROP) of l-lactide (L-LA) still requires the use of highly active and thermally stable metal-based catalysts, which have raised some environmental concerns. While the excellent balance between activity and functional group compatibility of organic acid catalysts makes them some of the most suitable catalysts for the metal-free ROP of L-LA, the majority of these acids are highly volatile and subject to decomposition at high temperature, which limits their use under industrially relevant conditions. In this work we exploit the use of a nonstoichiometric acid–base organocatalyst to promote the solvent-free and metal-free ROP of L-LA at elevated temperatures in the absence of epimerization and transesterification. To do so, a stable acidic complex was prepared by mixing 4-(dimethylamino)pyridine (DMAP) with 2 equiv of methanesulfonic acid (MSA). Both experimental and computational results indicate that DMAP:MSA (1:2) not only is highly thermally stable but also promotes the retention of stereoregularity during the polymerization of L-LA, leading to PLLA with a molar mass of up to 40 kg mol–1 and a chiral purity in excess of 98%. This result provides a new feature to exploit in organocatalyzed polymerization and in the design of new catalysts to facilitate the path to market.

Activation and Conjugation of Soluble Polysaccharides using 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate (CDAP)

Conjugate vaccines are remarkable advances in vaccinology. For the preparation of polysaccharide conjugate vaccines, the polysaccharides can be conveniently functionalized and linked to vaccine carrier proteins using 1-cyano-4-dimethylaminopyridine tetrafluoroborate (CDAP), an easy-to-handle cyanylating reagent. CDAP activates polysaccharides by reacting with carbohydrate hydroxyl groups at pH 7-9. The stability and reactivity of CDAP are highly pH-dependent. The pH of the reaction also decreases during activation due to the hydrolysis of CDAP, which makes good pH control the key to reproducible activation. The original CDAP activation protocol was performed at room temperature in unbuffered pH 9 solutions. Due to the rapid reaction under this condition (<3 min) and the accompanying fast pH drop from the rapid CDAP hydrolysis, it was challenging to quickly adjust and maintain the target reaction pH in the short time frame. The improved protocol described here is performed at 0 °C, which slows CDAP hydrolysis and extends the activation time from 3 min to ~15 min. Dimethylaminopyridine (DMAP) was also used as a buffer to pre-adjust the polysaccharide solution to the target activation pH before adding the CDAP reagent. The longer reaction time, coupled with the slower CDAP hydrolysis and the use of DMAP buffer, makes it easier to maintain the activation pH for the entire duration of the activation process. The improved protocol makes the activation process less frenetic, more reproducible, and more amenable to scaling up.

Activation and Conjugation of Soluble Polysaccharides using 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate (CDAP).

Conjugate vaccines are remarkable advances in vaccinology. For the preparation of polysaccharide conjugate vaccines, the polysaccharides can be conveniently functionalized and linked to vaccine carrier proteins using 1-cyano-4-dimethylaminopyridine tetrafluoroborate (CDAP), an easy-to-handle cyanylating reagent. CDAP activates polysaccharides by reacting with carbohydrate hydroxyl groups at pH 7-9. The stability and reactivity of CDAP are highly pH-dependent. The pH of the reaction also decreases during activation due to the hydrolysis of CDAP, which makes good pH control the key to reproducible activation. The original CDAP activation protocol was performed at room temperature in unbuffered pH 9 solutions. Due to the rapid reaction under this condition (<3 min) and the accompanying fast pH drop from the rapid CDAP hydrolysis, it was challenging to quickly adjust and maintain the target reaction pH in the short time frame. The improved protocol described here is performed at 0 °C, which slows CDAP hydrolysis and extends the activation time from 3 min to ~15 min. Dimethylaminopyridine (DMAP) was also used as a buffer to pre-adjust the polysaccharide solution to the target activation pH before adding the CDAP reagent. The longer reaction time, coupled with the slower CDAP hydrolysis and the use of DMAP buffer, makes it easier to maintain the activation pH for the entire duration of the activation process. The improved protocol makes the activation process less frenetic, more reproducible, and more amenable to scaling up.

Ionic cobalt complexes derived from an amine-bis(benzotriazole phenolate) ligand as bifunctional catalysts for copolymerization of epoxides and anhydrides

This study reports that a series of structurally well-defined mono- and di-nuclear cobalt complexes containing the amine-bis(benzotriazole phenolate) ligand (amine-BiBTP) have been synthesized and fully characterized. The one-pot reaction of the amine-BiBTP ligand precursor with cobalt nitrate salt in the presence of triethylamine under refluxing methanolic solution generated di-nuclear cobalt(II) complexes [(C1NNBiBTP)2Co2] (1). The mono-Co(II) complex [(C1NNBiBTP)CoR] (R = DMAP (2), tBuPy (3)) could be prepared by 1 with a stoichiometric amount of 4-(dimethylamino)pyridine (DMAP) or 4-tert-butylpyridine (tBuPy) to yield a five-coordinated mononuclear cobalt species. Interestingly, the Co(III) complexes 4–7 resulted from the treatment of 2 or 3 with silver nitrate/trifluoroacetate as the oxidizing agent, and an ionic and mononuclear species formulated as [(C1NNBiBTP)CoR2]X (R = DMAP, X = NO3 (4), R = DMAP, X = CF3COO (5), R = tBuPy, X = NO3 (6), R = tBuPy, X = CF3COO (7)) could be formed. Versatile catalysis towards copolymerization of internal epoxides with anhydride catalyzed by these Co(II)/Co(III) was systematically studied under mild conditions. Experimental results revealed that complex 4 was shown to effectively catalyze copolymerization of cyclohexene oxide (CHO) with phthalic anhydride (PA), resulting in copolymers with a high alternating microstructure possessing ≥ 99% ester-linkage contents.

Synergistic Dual Catalytic System and Kinetics for the Alcoholysis of Poly(Lactic Acid)

Plastic pollution is a global issue that is approaching crisis levels as plastic production is projected to reach 1.1 GT annually by 2050. The bioplastic industry along with a circular production economy are solutions to this problem. One promising bioplastic polylactic acid (PLA) has mechanical properties comparable to polystyrene (PS), so it could replace PS in its applications as a more environmentally sustainable material. However, since the bioplastic PLA also suffers from long biodegradation times in the environment, to ensure that it does not add to the current pollution problem, it should instead be chemically recycled. In this work, PLA was chemically recycled via alcoholysis, using either methanol or ethanol to generate the value-added products methyl lactate and ethyl lactate respectively. Two catalysts, zinc acetate dihydrate (ZnAc) and 4-(dimethylamino)pyridine (DMAP), were tested both individually and in mixtures. A synergistic effect was exhibited on the reaction rate when both catalysts were used in an equal ratio. The methanolysis reaction was determined to be two-step, with the activation energy estimated to be 73 kJ mol−1 for the first step and 40.16 kJ mol−1 for the second step. Both catalysts are cheap and commercially available, their synergistic effect could be exploited for large-scale PLA recycling.

Heterocyclic-Additive-Activated Dinuclear Dysprosium Electrocatalysts for Heterogeneous Water Oxidation.

Heterogeneous catalysis based on air-stable lanthanide complexes is relatively rare, especially for electrochemical water oxidation and reduction. Therefore, it is highly desired to investigate the synergy caused by cocatalysts on the lanthanide complex family for heterogeneous catalysis because of their structural diversity, air/moisture insensitivity, and easy preparation under an air atmosphere. Two mononuclear and three dinuclear dysprosium complexes containing a series of Schiff-base ligands have been demonstrated as robust electrocatalysts for triggering heterogeneous water oxidation in alkaline solution, in which the complex [Dy2(hmb)2(OAc)4]·MeCN(3) was revealed to have the best activity toward heterogeneous water oxidation among all five complexes in the present study. The molecular activation of dysprosium complexes has also been investigated with a series of N-containing heterocyclic additives [i.e., 4-(dimethylamino)pyridine (DMAP), bis(triphenylphosphine)iminium chloride ([PPN]Cl), indole, and quinoline]. In particular, the corresponding overpotential was effectively enhanced by 211 mV (at a current density of 10 mA cm-2) with the assistance of DMAP. On the basis of electrochemical and ex situ/in situ spectroscopic investigations, the best catalyst, DMAP-complex 3 on a carbon paper electrode, was confirmed with well-maintained molecular identity during heterogeneous water oxidation free of forming any dysprosium oxide and/or undesired products.

Dialkylboryl-Substituted Cyclic Disilenes Synthesized by Desilylation-Borylation of Trimethylsilyl-Substituted Disilenes.

π-Electron systems of silicon have attracted attention because of their narrow HOMO-LUMO gap and high reactivity, but the structural diversity remains limited. Herein, new dialkylboryl-substituted disilenes were synthesized by the selective desilylation-borylation of the corresponding trimethylsilyl-substituted disilenes. The dialkylboryl-substituted disilenes were fully characterized by a combination of NMR spectroscopy, MS spectrometry, single-crystal X-ray diffraction analysis, and theoretical calculations. The longest-wavelength absorption bands of boryldisilenes were bathochromically shifted compared to the corresponding silyl-substituted disilenes, indicating a substantial conjugation between π(Si=Si) and vacant 2p(B) orbitals. In the presence of 4-(dimethylamino)pyridine (DMAP), the dialkylboryl groups in the boryl-substituted disilenes were easily converted to trimethylsilyl groups, suggesting the dialkylboryl-substituted disilenes in the presence of a base serve as the surrogates of disilenyl anions (disilenides).

A Novel BODIPY Quaternary Ammonium Salt-Based Fluorescent Probe: Synthesis, Physical Properties, and Live-Cell Imaging.

The development of biological fluorescent probes is of great significance to the field of cancer bio-imaging. However, most current probes within the bulky hydrophobic group have limited application in aqueous medium and restricted imaging under physiological conditions. Herein, we proposed two efficient molecules to study their physical properties and imaging work, and the absorption and fluorescence intensity were collected with varying ions attending in aqueous medium. We enhance the water solubility through the quaternization reaction and form a balance between hydrophilic and hydrophobicity with dipyrrome-theneboron difluoride (BODIPY) fluorophore. We introduced pyridine and dimethylaminopyridine (DMAP) by quaternization and connected the BODIPY fluorophore by ethylenediamine. The final synthesized probes have achieved ideal affinity with HeLa cells (human cervical carcinoma cell line) in live-cell imaging which could be observed by Confocal Microscope. The probes also have a good affinity with subcutaneous tumor cells in mice in in vivo imaging, which may make them candidates as oncology imaging probes.

Fluorometric detection of fluoride and thiocyanate ions using novel anthrapyrazolone derivatives

Anion recognition and sensing via artificial receptors have attracted a great deal of attention due to their significant role in chemical, biological, medical, and environmental applications. In the present investigation, we have demonstrated facile and straightforward synthesis of three low molecular weight fluorophore molecules designated as 2,7 - dihydrobenzo [1,2,3 - cd:4,5,6-c'd']bis(indazole) [DHBBI], 2-(benzo[1,2,3-cd:4,5,6-c'd']bis(indazole)-2(7H)-yl)ethanol [DHBBI-OH] and 2-(benzo[1,2,3-cd:4,5,6-c'd']bis(indazole)-2(7H)-yl)ethyl methacrylate [DHBBI-MA] for the fluorometric detection of fluoride and thiocyanate ions in solution phase. DHBBI was synthesized by a condensation reaction of 1,5-dichloroanthraquinone with hydrazine monohydrate. DHBBI-OH was synthesized by the reaction of DHBBI with 2-bromoethanol using K 2 CO 3 as base whereas, DHBBI-MA was synthesized by the reaction of DHBBI-OH with methacrylic anhydride using dimethylamino pyridine (DMAP). Novel three molecules were characterized by 1 H NMR, FT-IR, HR-MS and UV–Vis spectroscopy. The strong fluorescence nature of the compounds was further analyzed towards the detection of different ions. All the compounds DHBBI, DHBBI-OH, and DHBBI-MA showed turn on fluorescence behavior for fluoride (F - ) ion and turn off fluorescence behavior for thiocyanate (SCN - ) ion respectively.

Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst.

A new triazinedione-based reagent, (N,N'-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.

Machine Learning Assisted Discrimination of 20 Volatile Organic Compounds with Response Prediction Via UNIFAC Modeling

Accurate detection of volatile organic compounds (VOCs) in complex background plays an important role in both natural and human-related activities, such as environmental protection, medical screening, food safety, and homeland security. Reliable monitoring of atmospheric VOCs is vital because vapor exposure can accelerate air-borne toxic generation and lead to tropospheric air pollution. While conventional analytical instruments such as gas chromatography-mass spectrometry (GC-MS) are largely used for identification of unknown VOCs, it is desirable for sensing technology to transition into a low cost, energy-efficient, and miniaturized media that can be implemented into personal devices.As one of the fastest growing types of chemical sensors, chemiresistors possess many desirable characteristics such as straightforward fabrication and easy to integrate. Sensing responses for nanoparticle-based chemiresistor are based on the sorbent-phase interaction of an analyte with the sensing materials, which can be explained by a thermally activated electron tunneling mechanism. The morphology of the gold-nanoparticle (AuNP) assembly (i.e. the interparticle distance) between the electrodes determines the baseline resistance of that individual sensor element.In this work, we demonstrate the detection and classification of 20 VOC vapors at room temperature using a multi-AuNP chemiresistor array fabricated with gold nanoparticles with chemically diverse ligands, including 4-(dimethylamino)pyridine (DMAP), tetradecylamine (TDA), and 4-aminothiophenol (4-ATP). The castellated electrode structures were fabricated using standard photolithography and liftoff processes. Classification accuracy was determined using a machine learning algorithm on a matrix of sensing response data. Supervised classifiers applied in this work include linear discriminant analysis (LDA), support vector machine (SVM), k-nearest neighbors (KNN), and random forest (RF). The results demonstrated that pattern recognition accuracy increases when a combination of ligands was used, as compared to sensors with one type of ligand. This proof-of-concept study illustrated that we were able to improve classification accuracy by choosing ideal sensing elements with optimized built-in redundancy. Meanwhile, a vapor sorption model was established to predict the chemiresistive sensor responses. One of the biggest challenges of AuNP-based chemiresistive sensor technology is finding the best candidates of materials that provide sufficient resolving power to differentiate chemicals in complex surroundings for molecular pattern recognition. To evaluate the sensor performance of ligand-analyte interactions, a UNIFAC (UNIQUAC Functional-group Activity Coefficients) model was established in this study to predict the sorption between a certain ligand material and VOC vapors. Therefore, a more performance-efficient sensing element library can be established for different types of analytes. Specifically, partition coefficients were determined from the UNIFAC method, and the sorbent phase concentration was obtained from modified Raoult’s Law. To validate our model, simulated UNIFAC partition coefficients were compared with experimental results and data reported from literature. Besides sensor responses, other characteristic parameters of chemiresistor performance are also studied, including sensitivity, sensitivity ratio, volumetric sensitivity, and molar sensitivity. This work illustrated the versatility of gold nanoparticle-based chemiresistor array systems for VOC detection, discrimination, and sensor signal prediction. Figure 1

Conversion of CO2 into Chloropropene Carbonate Catalyzed by Iron (II) Phthalocyanine Hypercrosslinked Porous Organic Polymer.

Commercial iron (II) phthalocyanine (FePc) was knitted with biphenyl using a Friedel–Crafts reaction to yield a micro-meso porous organic polymer (FePc-POP) with a specific surface area of 427 m2/g and 5.42% of iron loading. This strategy allowed for the direct synthesis of a heterogeneous catalyst from an iron containing monomer. The catalytic system, formed by the knitted polymer containing FePc and DMAP (4-dimethylamino pyridine) as base, results in an efficient heterogeneous catalyst in the cycloaddition of CO2 to epichlorohydrin to selectively obtain the corresponding cyclic carbonate. Thus, a TON (mmol substrate converted/mmol catalysts used) value of 2700 was reached in 3 h under mild reaction conditions (solvent free, 90 °C, 3 bar of CO2). The catalyst does not exhibit leaching during the reactions, which was attributed to the excellent stability of the metal in the macrocycle.

Chromium Diamino-bis(phenolate) Complexes as Catalysts for the Ring-Opening Copolymerization of Cyclohexene Oxide and Carbon Dioxide.

Chromium diamino-bis(phenolate) complexes, CrXL [where L = 6,6'-((1,4-diazepane-1,4-diyl)bis(methylene))bis(2,4-dimethylphenolato) and X = Cl- (1), OH- (2), and N3- (3)], were prepared and characterized by MALDI-TOF MS and single-crystal X-ray diffraction. Complex 1 crystallized as two linkage isomers, specifically a green chloride-bridged dimer (1) and a pink asymmetrically bridged isomer exhibiting one chloride bridging atom and one bridging phenolate oxygen (1'). Adventitious moisture during sample handling causes the formation of hydroxide-containing complex 2. The reaction of 1 with PPNN3 (where PPN = bis(triphenylphosphine)iminium) permits the isolation of a crystalline chromium azide complex, 3, which was structurally authenticated. Complex 1 showed good activity toward the ring-opening copolymerization of cyclohexene oxide and carbon dioxide with an added chloride, azide, or 4-(dimethylamino)pyridine (DMAP) cocatalyst to give a completely alternating polycarbonate with a narrow molecular weight dispersity.

Crystal structure of 4-(dimethylamino)pyridin-1-ium-2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-bis(olate) 4-dimethylaminopyridine (2:1) water undeca-solvate

The structure of the title compound, 4-(dimethylamino)pyridin-1-ium-2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-bis(olate) 4-dimethylaminopyridine water undeca-solvate, C57H87Cl5N12O21, obtained from interaction between chloranilic acid (caH2), and dimethyl aminopyridine (DMAP) has been determined by single crystal X-ray diffraction. The title compound, (DMAPH)5(ca)2.5·(DMAP)·11H2O, crystallized in the triclinic crystal system with space group, P (no. 2), a = 13.3824(15) Å, b = 13.4515(17) Å, c = 19.048(2) Å, α = 86.014(4)°, β = 88.821(4)°, γ = 86.367(4)°, V = 3413.3(7) Å3, Z = 2, T = 100(2) K, μ(MoKα) = 0.294 mm-1, Dcalc = 1.414 g/cm3, 59413 reflections measured (3.76° ≤ 2Θ ≤ 56°), 16405 unique (Rint = 0.0517, Rsigma = 0.0589) which were used in all calculations. The final R1 was 0.0460 (I ≥ 2σ(I)) and wR2 was 0.1271 (all data). Using supramolecular chemistry principles, proton donors (chloranilic acid) and acceptor (DMAP) were combined to generate a multicomponent hydrogen-bonded system. Due to the presence of protonated bases (DMAPH+), the dominant interactions are the N+-H···O hydrogen bonds, whereas the negative charges of an acceptor from the chloranilate dianion (ca2-) are delocalized. Additionally, three sets of water clusters in the title compound were identified, namely a cyclic pentamer, a linear, and an acute-shaped trimer water cluster. It was further observed that strong hydrogen bond interactions occurred between the solvated aqua molecule(s) acting as a proton donor and the neutral DMAP acting as a proton acceptor. The crystal packing is further stabilized by O-H···Cl and C-H···Cl weak halogen interactions. The lattice metric strength is further held by observed π-π stacking interactions (centroid-centroid) with inter centroid distances between sets of the DMAPH rings of 3.624(3), 3.642(4), 3.739(3), 3.863(3) and 3.898(3) Å, respectively.