Ethanol Solvate Research Articles

Crystal structures and circular dichroism of {2,2′-[(1S,2S)-1,2-diphenylethane-1,2-diylbis(nitrilophenylmethanylylidene)]diphenolato}nickel(II) and its ethanol solvate

The title compound, [Ni(C40H30N2O2)] (1), with an optically active Schiff base ligand derived from 2-hydroxybenzophenone and (1S,2S)-1,2-diphenylethylenediamine, was crystallized as the solvent-free and ethanol solvate forms (1 and 1·2C2H5OH). In both structures, the two phenyl groups on the stereogenic centers of the O,N,N,O-tetradentate ligand are axially oriented, and the conformation of the central diamine chelate ring is λ. The circular dichroism (CD) spectra of 1 and the analogous nickel(II) complex [Ni(C30H26N2O2)] (2) in solution show partially similar patterns in the 350–450 nm range, but are mirror images in the longer wavelength region (450–650 nm). In the latter region, the sign of CD for these complexes is sensitive to the substituents on the C=N carbon atoms (phenyl for 1 and methyl for 2) rather than the diamine chelate ring conformation.

Synthesis and crystal structure of poly[[μ-chlorido-μ-(2,3-di-methyl-pyrazine)-copper(I)] ethanol hemisolvate], which shows a new isomeric CuCl(2,3-di-methyl-pyrazine) network.

Reaction of copper(I)chloride with 2,3-di-methyl-pyrazine in ethanol leads to the formation of the title compound, poly[[μ-chlorido-μ-(2,3-di-methyl-pyrazine)-copper(I)] ethanol hemisolvate], {[CuCl(C6H8N2)]·0.5C2H5OH} n or CuCl(2,3-di-methyl-pyrazine) ethanol hemisolvate. Its asymmetric unit consists of two crystallographically independent copper cations, two chloride anions and two 2,3-di-methyl-pyrazine ligands as well as one ethanol solvate mol-ecule in general positions. The ethanol mol-ecule is disordered and was refined using a split model. The methyl H atoms of the 2,3-di-methyl-pyrazine ligands are also disordered and were refined in two orientations rotated by 60° relative to each other. In the crystal structure, each copper cation is tetra-hedrally coordinated by two N atoms of two bridging 2,3-di-methyl-pyrazine ligands and two μ-1,1-bridg-ing chloride anions. Each of the two copper cations are linked by pairs of bridging chloride anions into dinuclear units that are further linked into layers via bridging 2,3-di-methyl-pyrazine coligands. These layers are stacked in such a way that channels are formed in which the disordered solvent mol-ecules are located. The topology of this network is completely different from that observed in the two polymorphic modifications of CuCl(2,3-di-methyl-pyrazine) reported in the literature [Jess & Näther (2006). Inorg. Chem. 45, 7446-7454]. Powder X-ray diffraction measurements reveal that the title compound is unstable and transforms immediately into an unknown crystalline phase.

Molecular spectroscopy, solvent effect, and DFT studies of azithromycin solvate

Azithromycin ethanol solvate monohydrate [C38H72N2O120.5(C2H6O)H2O], abbreviated by AZM-MH-EtOH, was synthesized by slow evaporation method and investigated by powder X-ray diffraction, Raman and infrared (IR) spectroscopy combined with density functional theory (DFT) studies. Electronic and vibrational properties were properly investigated based on a theoretical study of solvation effects, using implicit solvation and solute electron density models. The electronic and vibrational studies were evaluated under aqueous, ethanolic, and vacuum conditions. The electronic structure calculations indicated that the AZM-MH-EtOH is chemically more stable in solvents compared to vacuum condition. Ultraviolet–visible (UV–vis) measurements confirmed the stability of the material in ethanolic medium, due to higher absorbance values compared to the aqueous medium. Vibrational changes were observed in the Raman and IR bands, which have connection with hydrogen bonds. The experimental vibration modes showed better accordance with the predicted modes’ values under solvation effects, but a slight divergence is noticed when we compared to vibration modes obtained in vacuum. Furthermore, the results have revealed a greater affinity profile of AZM-MH-EtOH for water and ethanol solvents compared to theoretical data under vacuum condition.

Ethanol Solvation of Polymer Residues in Graphene Solution-Gated Field Effect Transistors.

The persistence of photoresist residues from microfabrication procedures causes significant obstacles in the technological advancement of graphene-based electronic devices. These residues induce undesired chemical doping effects, diminish carrier mobility, and deteriorate the signal-to-noise ratio, making them critical in certain contexts, including sensing and electrical recording applications. In graphene solution-gated field-effect transistors (gSGFETs), the presence of polymer contaminants makes it difficult to perform precise electrical measurements, introducing response variability and calibration challenges. Given the absence of viable short to midterm alternatives to polymer-intensive microfabrication techniques, a postpatterning treatment involving THF and ethanol solvents was evaluated, with ethanol being the most effective, environmentally sustainable, and safe method for residue removal. Employing a comprehensive analysis with XPS, AFM, and Raman spectroscopy, together with electrical characterization, we investigated the influence of residual polymers on graphene surface properties and transistor functionality. Ethanol treatment exhibited a pronounced enhancement in gSGFET performance, as evidenced by a shift in the charge neutrality point and reduced dispersion. This systematic cleaning methodology holds the potential to improve the reproducibility and precision in the manufacturing of graphene devices. Particularly, by using ethanol for residue removal, we align our methodology with the principles of green chemistry, minimizing environmental impact while advancing diverse graphene technology applications.

Sumatriptan Succinate Hemi(Ethanol Solvate)

1-(3-(2-(Dimethylammonio)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate (sumatriptan succinate, HSum+·HSucc−) is a serotonin receptor agonist used to treat migraines. By the recrystallization of this substance from ethanol, its hemi(ethanol solvate), HSum+·HSucc−·0.5EtOH, was obtained. The solid was characterized by X-ray diffraction and FT-IR spectroscopy. In HSum+·HSucc−·0.5EtOH, solvent molecules link succinate anions into infinite O–H…O bonded chains, which are further connected by N–H…O interactions with cations into H-bonded layers.

A comprehensive analysis of the molecular packing in the crystal of N2-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine and in its 1:1 ethanol solvate

The crystal and molecular structures of N2-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine (1) and its 1:1 ethanol solvate (1.EtOH) are reported. The triazine molecule is substituted by amino, 3,4,5-trimethoxyphenyl and 4-chlorophenylamino groups. The experimental molecular structures are like each other and similar to the calculated gas-phase structure. The molecular packing is distinct in that a twisted supramolecular tape is formed in 1 featuring amino-NH···N (triazine) hydrogen bonds. Similar hydrogen-bonding is evident in 1.EtOH but occurs between centrosymmetrically related molecules. The solvent ethanol molecule plays a pivotal role in the packing by participating amino-NH···O (ethanol) and ethanol-OH···O (methoxy) hydrogen bonds within a jagged supramolecular tape. Many additional non-covalent interactions between the tapes are noted in the three-dimensional molecular packing. These and the conventional hydrogen-bonding interactions have been evaluated by a variety of computational chemistry techniques. The greater crystal lattice energy calculated for 1.EtOH is ascribed to the stability afforded by the additional hydrogen-bonding involving the ethanol molecule and the considerably greater role of π···π stacking interactions in the molecular packing.

Structural, physicochemical characterization and antimicrobial activities of a new tris(8-quinolinolato-κ2N,O)cobalt(III) ethanol solvate [Co(C9H6NO)3].(C2H6O)

We report herein the synthesis and physicochemical characterization of a new 8-hydroxyquinoline cobalt(III) complex ethanol solvate with formula [Co(C9H6NO)3].(C2H6O). This compound was been prepared by slow evaporation at room temperature and characterized by single crystal X-ray diffraction. It crystallizes in the monoclinic system, spaces group P21/n. The central cobalt ion has a slightly distorted square bipyramidal environment, coordinated by three chelating 8-hydroxyquinoline molecules. Structural cohesion is primarily established by π-π interactions between the neighboring rings of quinoline groups and intermolecular hydrogen bonds O-H…O connecting the cobalt complex entities and uncoordinated ethanol molecules.The title compound has been characterized by the infrared (IR) and the UV–Visible (UV–Vis) spectra. Intermolecular interactions in the crystal structure were quantified by Hirshfeld surface analysis. The band gap of the complex was calculated using solid-state reflectance spectra, and the results show that the complex acts as a semiconductor. Moreover, the new compound exhibits high antibacterial and antifungal activities, as detected by the well agar diffusion against various bacterial and fungal clinical strains. The superior inhibitory effect was observed against Klebsiella pneumoniae, Candida albicans and Candida glabrata with zones inhibition of about 17.5, 17.5 and 17 mm, respectively.

Solubility determination, dissolution properties and solid transformation of resmetirom (form A) in heptane and seven alcohols.

In this work, the solubility of resmetirom (form A) was initially measured in heptane and seven alcohol solvents by gravimetric methods. Then, the transformation temperature between form A and ethanol solvate was determined at 333.76 K. Subsequently, some commonly used models were applied to fit the solubility data, and it was found that the modified Apelblat equation and the Jouyban-Acree-van't Hoff (J-A-V) model achieved the highest correlation accuracy for those in mono-solvents and heptane + propanol, respectively. And the average relative deviation (ARD) values of models were less than 0.5%, indicating a good agreement with the experimental results. Additionally, through density functional theory calculation and the analysis of solvent parameters, it was observed that hydrogen-bonding played primary roles in the dissolution process of resmetirom. The multiple factors such as the polarity of solvent, active site interaction, the molecular size and free volume all affect the solubility of resmetirom. Furthermore, by comparing the experimental and simulated infrared spectra of form A and two alcohol solvates, five characteristic bands were selected for quantification. Partial least squares regression (PLSR), a multivariate statistical analysis method, was used to extract quantitative information. The quantitative analysis model was established based on specific wavelength intervals, which were associated with inter-molecular interactions. Combined with PLSR, a new high-precision quantitative method was established to study the solid transformation process between form A and solvates. From 303.15 to 323.15 K, the rate of transformation from form A to methanol solvate or ethanol solvate was decreased with increasing temperature, revealing that the transformation process was driven by the solubility difference between form A and solvates under the studied conditions. This research will definitely afford necessary solubility data and solvent selection for the design of the crystallization process of resmetirom (form A) in industry, and provide basic data for the production of resmetirom (form A) in the pharmaceutical industry.

Synthesis and Structure of a Host-Guest Inclusion System between C-propyl-o-toluidine-methyl-resorcin[4]arene and Ethanol Solvate

Synthesis and Structure of a Host-Guest Inclusion System between C-propyl-o-toluidine-methyl-resorcin[4]arene and Ethanol Solvate

Discovered two polymorphs and two solvates of lamotrigine-tolfenamic acid salt: Thermal behavior and crystal morphological differences

Multi-component pharmaceutical systems such as cocrystal and salt have gained popularity in academia and industry due to their ability to regulate the poor physicochemical properties of active pharmaceutical ingredients (APIs). However, different crystal states, namely polymorphs are becoming a key factor influencing future clinical drug safety. It remains an under explored field, particularly how to hit the polymorphs of multi-components system quickly and effectively. For the first time, a novel drug-drug salt of lamotrigine (LAM)-tolfenamic acid (TOL) with two polymorphs and two solvates were discovered in this study. Forms I and II exist in rhombohedral and block crystal morphologies, whereas methanol and ethanol solvates are crystallized as rods and flakes, respectively. Further physicochemical properties were characterized and compared between parent compounds and the four crystal forms. The apparent solubilities of the new four crystal forms were higher than TOL but lower than LAM. The intrinsic dissolution rates of all crystal forms at 37.0 °C followed a similar trend, and all crystal forms were non-hygroscopic (<1.0%). Two stable polymorphs provide a new choice for the further formulation development.

Insight into the Crystal Structures and Potential of Two Newly Synthesized Naproxen-Based Hydrazide Derivatives as Potent COX-2 Inhibitors.

Although nonsteroidal anti-inflammatory drugs (NSAIDs) are medicines that are widely used to relieve pain, reduce inflammation, and bring down high temperature, literature confirmed that they still have harmful side effects. Most of their side effects are in the digestive system due to the carboxylic group. As naproxen is one of the NSAIDs, in this work, we try to mask the carboxylic group in naproxen with a relatively safe functional group. So, herein, we report the synthesis of new naproxen-based hydrazones derivatives, namely, (E)-N'-1-(4-chlorophenyl)ethylidene)-2-(6-methoxynaphthalen-2-yl)propane hydrazide (4a) and (E)-N'-(4-hydroxybenzylidene)-2-(6-methoxynaphthalen-2-yl)propane hydrazide ethanol solvate (4b). The compounds were confirmed by X-ray diffraction studies. Hirshfeld surface analyses and energy frameworks of 4a and 4b have been carried out and blind molecular docking studies of them to the COX-2 enzyme were undertaken to obtain binding affinities for judging whether the compounds could act as anti-inflammatory agents. The compounds interact with the key residues: Arg120, Val349, Leu352, Tyr355, Val523, Ala527, Ser530, and Leu531 of the active enzyme pocket. Molecular dynamics studies predicted that the complexes of 4a and 4b with COX-2 are structurally stable and no major conformational changes were observed. Confirmation of the docking and simulation data was achieved by a binding free energies analysis that indicated the dominance of van der Waals energy. The compounds are drug-like molecules as they obey all prominent drug-like rules and have acceptable pharmacokinetic profiles. To investigate the relationship between their intrinsic electronic properties and their possible similarities to actual drugs, the gas-phase DFT optimizations and NBO analyses were also performed in this study.

3-aminoquinoline: a turn-on fluorescent probe for preferential solvation in binary solvent mixtures

3-Aminoquinoline (3AQ) has been used as a fluorescent probe for preferential solvation in hexane-ethanol solvent mixtures. Results of the present experiment have been put into context by comparison with prior observations with 5-aminoquinoline (5AQ) as the probe. 3AQ exhibits a relatively small change of dipole moment (Δμ = 2.2 D) upon photoexcitation, compared to 5AQ (Δμ = 6.1D), which might appear to be a hindrance in the way of its use as a solvation probe. Indeed, the values of parameters like spectral shifts are smaller for the present experiment with 3AQ. At the smallest concentration of alcohol used, its local mole fraction around the probe is significantly lower than in the previous experiments with 5AQ. However, these apparent disadvantages are outweighed by the significant increase in fluorescence intensity and lifetime observed with increasing concentration of ethanol in the solvent mixture, as opposed to the drastic fluorescence quenching that occurs for 5AQ. This is a marked advantage in the use of 3AQ in studies like the present one. The local mole fraction of ethanol and preferential solvation index experienced by 3AQ are in line with those reported for 5AQ. The disadvantage of the smaller magnitude of Δμ persists in the time resolved fluorescence experiments, for solvent mixtures with very low ethanol content. Negligible wavelength dependence of fluorescence transients of 3AQ is observed for x p = 0.002,. However, this effect is outweighed at higher alcohol concentrations, for which nanosecond dynamics of preferential solvation is observed.

Insights into the ethanol solvate form of clarithromycin

Some polymorphic drugs may undergo solid-state transformations as a result of storage and manufacturing processes, which could have a significant impact on the performance characteristics of the drug. The present study was conducted as a strategy to provide information on clarithromycin polymorphs. The exhaustive characterization of solid form 0, an ethanol solvate, was performed starting with the development of a new synthesis route. The structural characterization was carried on by comparing the form 0 with the form II, the one currently used on the market. A variety of techniques, such as solid state nuclear magnetic resonance, X-ray powder diffraction, infrared spectroscopy, thermoanalytical methods and confocal microscopy, were used to identify the form 0. These studies revealed important intermolecular interactions, as well as certain spatial and morphological particularities. The biopharmaceutical properties including solubility in water and simulated gastric fluid, and microbiological performance were investigated. The physical stability under normal storage conditions during 15 months was examined, revealing a desolvation process and a subtle polymorphic transformation. The studies performed on the ethanol solvate of clarithromycin could prove to be a useful tool for assays used to ensure that the drug quality remains without changes in the final dosage product.

A new pseudopolymorph of berberine chloride: crystal structure and Hirshfeld surface analysis.

A new pseudopolymorph of berberine, 9,10-dimeth-oxy-5,6-di-hydro-2H-7λ5-[1,3]dioxolo[4,5-g]iso-quinolino-[3,2-a]isoquinolin-7-ylium chloride methanol monosolvate, C20H18NO4 +·Cl-·CH3OH, was obtained during co-crystallization of berberine chloride with malonic acid from methanol. The berberine cations form dimers, which are further packed in stacks. The title structure was compared with other reported solvates of berberine chloride: its dihydrate, tetra-hydrate, and ethanol solvate hemihydrate. Hirshfeld analysis was performed to show the inter-molecular inter-actions in the crystal structure of the title compound, and its fingerprint plots were compared with those of the already studied solvates.

Structural studies of various olmesartan solvates.

Seven solvates of the angiotensin II receptor blocker agent olmesartan (C24H26N6O3), namely, the methanol (C24H26N6O3·CH4O), ethanol (C24H26N6O3·C2H6O), isopropanol (C24H26N6O3·C3H8O), isobutanol (C24H26N6O3·C4H10O), 2-ethoxyethanol (C24H26N6O3·C4H10O2), chloroform (C24H26N6O3·CHCl3) and acetonitrile (C24H26N6O3·C2H3N) solvates, were successfully obtained. The crystal structures were determined using the single-crystal X-ray diffraction technique and the structural features are described, each solvate containing one molecule of olmesartan and one of solvent in the asymmetric unit. The samples were also analyzed by powder X-ray diffraction. Total lattice energies and binding energies between the olmesartan and solvent molecules were evaluated, which can be partitioned into electrostatic, polarization, dispersion and repulsion components. Hirshfeld and fingerprint plot analysis was performed to highlight the intermolecular contacts. Hydrogen bonding and supramolecular arrangements were comparatively studied for the seven solvates.

Structural Characterization of Multicomponent Crystals Formed from Diclofenac and Acridines.

Multicomponent crystals containing diclofenac and acridine (1) and diclofenac and 6,9-diamino-2-ethoxyacridine (2) were synthesized and structurally characterized. The single-crystal XRD measurements showed that compound 1 crystallizes in the triclinic P-1 space group as a salt cocrystal with one acridinium cation, one diclofenac anion, and one diclofenac molecule in the asymmetric unit, whereas compound 2 crystallizes in the triclinic P-1 space group as an ethanol solvate monohydrate salt with one 6,9-diamino-2-ethoxyacridinium cation, one diclofenac anion, one ethanol molecule, and one water molecule in the asymmetric unit. In the crystals of the title compounds, diclofenac and acridines ions and solvent molecules interact via N–H⋯O, O–H⋯O, and C–H⋯O hydrogen bonds, as well as C–H⋯π and π–π interactions, and form heterotetramer bis[⋯cation⋯anion⋯] (1) or heterohexamer bis[⋯cation⋯ethanol⋯anion⋯] (2). Moreover, in the crystal of compound 1, acridine cations and diclofenac anions interact via N–H⋯O hydrogen bond, C–H⋯π and π–π interactions to produce blocks, while diclofenac molecules interact via C–Cl⋯π interactions to form columns. In the crystal of compound 2, the ethacridine cations interact via C–H⋯π and π–π interactions building blocks, while diclofenac anions interact via π–π interactions to form columns.

Crystal structures of two Co(NCS)2 urotropine coordination compounds with different Co coordinations.

The reaction of Co(NCS)2 with urotropine in ethanol leads to the formation of two different compounds, namely, bis-(ethanol-κO)bis-(hexa-methyl-ene-tetra-mine-κN)bis-(thio-cyanato-κN)cobalt(II)-di-aqua-κ 2O-bis-(hexa-methyl-ene-tetra-mine-κN)bis-(thio-cyanato-κN)cobalt(II)-ethanol-hexa-methyl-ene-tetra-mine (1.2/0.8/1.6/4), [Co(NCS)2(C6H12N4)2(C2H6O)2]1.2·[Co(NCS)2(C6H12N4)2(H2O)2]0.8·1.6C2H6O·4C6H12N4, 1, and tris-(ethanol-κO)(hexa-methyl-ene-tetra-mine-κN)bis(thio-cyanato-κN)cobalt(II), [Co(NCS)2(C6H12N4)(C2H6O)3], 2. In the crystal structure of compound 1, two crystallographically independent discrete complexes are observed that are located on centres of inversion. In one of them, the Co cation is octa-hedrally coordinated to two terminal N-bonded thio-cyanate anions, two urotropine ligands and two ethanol mol-ecules, whereas in the second complex 80% of the coordinating ethanol is exchanged by water. Formally, compound 1 is a mixture of two different complexes, i.e. di-aqua-dithio-cyanato-bis-(urotropine)cobalt(II) and di-ethano-ldi-thio-cyanato-bis-(uro-trop-ine)cobalt(II), that contain additional ethanol and urotropine solvate mol-ecules leading to an overall composition of [Co(NCS)2(urotropine)2(ethanol)1.2(H2O)0.8·0.8ethanol·4urotropine. Both discrete complexes are linked by inter-molecular O-H⋯O and O-H⋯N hydrogen bonding and additional urotropine solvate mol-ecules into chains, which are further connected into layers. These layers combine into a three-dimensional network by pairs of centrosymmetric inter-molecular C-H⋯S hydrogen bonds. In the crystal structure of compound 2, di-thio-cyanato-(urotropine)tri-ethano-lcobalt(II), the cobalt cation is octa-hedrally coordinated to two terminal N-bonded thio-cyanate anions, one urotropine ligand and three ethanol mol-ecules into discrete complexes, which are located in general positions. These complexes are linked by inter-molecular O-H⋯N hydrogen bonding into layers, which are further connected into a three-dimensional network by inter-molecular C-H⋯S hydrogen bonding.

Solvent-induced conformational tuning of lysozyme protein adlayers on silica surfaces: A QCM-D and LSPR study

There is broad interest in functionalizing solid surfaces with lysozyme, which is a widely studied antimicrobial protein. To date, most efforts have focused on developing more effective immobilization schemes to promote lysozyme attachment in fully aqueous conditions, while there remains an outstanding need to understand how tuning the solution-phase conformational stability of lysozyme proteins can modulate adsorption behavior and resulting adlayer properties. Inspired by the unique conformational behavior of lysozyme proteins in water-ethanol mixtures, we conducted quartz crystal microbalance-dissipation (QCM-D) and localized surface plasmon resonance (LSPR) measurements to systematically investigate the adsorption behavior of lysozyme proteins onto silica surfaces across a wide range of water-ethanol mixtures. Our findings revealed that lysozyme adsorption behavior strongly depended on the ethanol fraction in a non-monotonic fashion and this trend could be rationalized by taking into account how competing effects of water and ethanol solvation influence solution-phase protein size and conformational stability. Integrated analysis of the QCM-D and LSPR measurement trends enabled quantitative determination of the solvent mass within lysozyme adlayers, which tended to decrease at higher ethanol fractions and supported that the hydrodynamic properties of lysozyme adlayers are mainly influenced by the degree of protein conformational flexibility as opposed to solvation effects alone.

Solvation of Ethanol, Phenol, and o-Methoxyphenol in Dilute Aqueous Solutions under Normal and Supercritical Conditions

The structure of 2 wt % aqueous solutions of ethanol, phenol, and o-methoxyphenol (guaiacol) was modeled in NVT ensemble using the classical molecular dynamics method at densities of 0.997 and 0.133 g/cm3 corresponding to the normal (298 K, 0.1 MPa) and supercritical (673 K, 23.0 MPa) conditions. The self-diffusion coefficients were calculated for individual components in solutions; the radial distribution functions were calculated for the oxygen atoms of water molecules, oxygen atoms of hydroxyl groups, and centers of mass in phenol molecules. The possibility of clusterization of solute molecules was analyzed. The data obtained suggest heterogeneity of solutions, in which clusters of different compositions and structures can exist. Clusterization of up to seven ethanol and phenol molecules can occur under normal conditions, and dimerization was detected under SC conditions. The structural features of solutions under normal and SC conditions were compared. The difference in the formation of hydration shells of ethanol and phenols molecules was demonstrated. Stable shells of water molecules form around ethanol molecules under normal conditions. For phenols, the solvation shells are unstable, with a pronounced tendency toward clusterization of organic molecules.

Hidden Solvates and Transient Forms of Trimesic Acid

This article discusses the formation of trimesic acid (TMA) solvates with ethanol, isopropyl alcohol and dimethylformamide via liquid-assisted grinding and slurry experiments. Through the use of X-ray diffraction methods, we highlight the formation of a new ethanol solvate of TMA that completes the series of alcohol solvates observed, a temperature-induced phase transition in the isopropyl alcohol solvate between 233 K and 243 K, and a transient 1:3 solvate with dimethylformamide that mimics a previously identified dimethylsulfoxide solvate. The alcohol structures possess a TMA framework that is geometrically similar where the intermolecular energies between TMA molecules are equivalent. We have observed that increasing the length of the alcohol induces an increase in the distortion of the TMA framework to accommodate the longer alkyl tails.