Benzyl Alcohol Research Articles

Mechanistic Insights into the Effects of Ureas and Monomers on the Ring-Opening Alternating Copolymerization of Epoxides and Anhydrides Catalyzed by Organic Base/Urea.

Aliphatic polyester is an important polyester material with good biocompatibility and degradability, which can be synthesized through ring-opening alternating copolymerization (ROAC) of epoxides and anhydrides. Herein, density functional theory (DFT) is used to explore the mechanism of ROAC of epoxides (propylene oxide (PO), styrene oxide (SO), epichlorohydrin (ECH), and cyclohexane oxide (CHO)) and phthalic anhydride (PA) catalyzed by bis(triphenylphosphine) ammonium chloride (PPNCl) and ureas. It was found that the ring-opening polymerization (ROP) of epoxides is the rate-controlling step, and the benzyl alcohol (BnOH) as the initiator has little effect on the polymerization activity, which was consistent with previous experimental results. Calculated comparisons of the ROAC activity of CHO/PA catalyzed by four different ureas indicate that as the Lewis acidity of the urea increased, the energy barriers of the copolymerization increased and the activity decreased. The main reason was that the strong hydrogen-bonding interactions stabilized the key intermediate of the rate-controlling step and inhibited subsequent monomer insertion. Based on this, a series of new ureas with higher catalytic activity were designed by introducing electron-donating substituents. In SO polymerization, increasing the Lewis acidity of urea can improve the SO regioselectivity. In addition, the monomer ECH with CH2Cl shows higher activity of ROAC than PO and SO, which could be ascribed to the fact that the strong electron-withdrawing Cl atom stabilizes the transition state in the rate-controlling step and reduces the reaction energy barrier.

Trialkoxysilane-Induced Iridium-Catalyzed para-Selective C–H Bond Borylation of Arenes

An ideal approach for the construction of aryl boron compounds is to selectively replace a C–H bond in arenes with a C–B bond, and controlling regioselectivity is one of the most challenging aspects of these transformations. Herein, we report an iridium-catalyzed trialkoxysilane protecting group-assisted regioselective C–H borylation of arenes, including derivatives of benzaldehydes, acetophenones, benzoic acids, benzyl alcohols, phenols, aryl silanes, benzyl silanes, and multi-functionalized aromatic rings are all well tolerated and gave the para -selective C–H borylation products in a short time without the requirement of inert gases atmosphere. The site-selective C–H borylation can be adjustable by installing the developed trialkoxysilane protecting group on different functional groups on one aromatic ring. Importantly, the preparation process of the trialkoxychlorosilane is efficient and scalable. Mechanistic and computational studies reveal that the steric hindrance of the trialkoxysilane protecting group plays a key role in dictating the para-selectivity.

Identification of transporters involved in aromatic compounds tolerance through screening of transporter deletion libraries.

Aromatic compounds are used in pharmaceutical, food, textile and other industries. Increased demand has sparked interest in exploring biotechnological approaches for their sustainable production as an alternative to chemical synthesis from petrochemicals or plant extraction. These aromatic products may be toxic to microorganisms, which complicates their production in cell factories. In this study, we analysed the toxicity of multiple aromatic compounds in common production hosts. Next, we screened a subset of toxic aromatics, namely 2-phenylethanol, 4-tyrosol, benzyl alcohol, berberine and vanillin, against transporter deletion libraries in Escherichia coli and Saccharomyces cerevisiae. We identified multiple transporter deletions that modulate the tolerance of the cells towards these compounds. Lastly, we engineered transporters responsible for 2-phenylethanol tolerance in yeast and showed improved 2-phenylethanol bioconversion from L-phenylalanine, with deletions of YIA6, PTR2 or MCH4 genes improving titre by 8-12% and specific yield by 38-57%. Our findings provide insights into transporters as targets for improving the production of aromatic compounds in microbial cell factories.

Engineering MPC-Assisted Heterojunctional Photo-Oxidation Tailored by Interfacial Design of a P-Modulated C3N4 Heterojunction for Improved Aerobic Alcohol Oxidation.

The creation of two-dimensional van der Waals (VDW) heterostructures is a sophisticated approach to enhancing photocatalytic efficiency. However, challenges in electron transfer at the interfaces often arise in these heterostructures due to the varied structures and energy barriers of the components involved. This study presents a novel method for constructing a VDW heterostructure by inserting a phosphate group between copper phthalocyanine (CuPc) and boron-doped, nitrogen-deficient graphitic carbon nitride (BCN), referred to as Cu/PO4-BCN. This phosphate group serves as a charge mediator, enabling effective charge transfer within the heterostructure, thus facilitating electron flow from BCN to CuPc upon activation. As a result, the photogenerated electrons are effectively utilized by the catalytic Cu2+ core in CuPc, achieving a conversion efficiency of 96% for benzyl alcohol (BA) and a selectivity of 98.8% for benzyl aldehyde (BAD) in the presence of oxygen as the sole oxidant and under illumination. Notably, the production rate of BAD is almost 8 times higher than that observed with BCN alone and remains stable over five cycles. The introduction of interfacial mediators to enhance electron transfer represents a pioneering and efficient strategy in the design of photocatalysts, enabling the proficient transformation of BA into valuable derivatives.

A Comparative Study on the Choice of the Support in the Elaboration of Photocatalysts for the Photooxidation of Benzyl Alcohol under Mild Conditions

In the quest to combat global warming, traditional thermal chemistry processes are giving way to selective photocatalysis, an eco-friendly approach that operates under milder conditions, using benign solvents like water. Benzaldehyde, a versatile compound with applications spanning agroindustry, pharmaceuticals, and cosmetics, serves as a fundamental building block for various fine chemicals. This study aims at enhancing benzaldehyde production sustainability by utilizing photooxidation of benzyl alcohol. Gold nanoparticle-based catalysts are renowned for their exceptional efficiency in oxidizing bio-based molecules. In this research, Au nanoparticles were anchored onto three distinct supports: TiO2, ZrO2, and graphitic carbon nitride (g-C3N4). The objective was to investigate the influence of the support material on the selective photocatalysis of benzyl alcohol. In the preparation of g-C3N4, three different precursors—melamine, urea, and a 50:50 mixture of both—were chosen to analyze their impact on catalyst performance. After 4 h of irradiation at 365 nm, operating under acidic conditions (pH = 2), the Au photocatalyst on graphitic carbon nitride support synthesized using urea precursor (Au@g-C3N4(urea)) displayed the optimal balance between conversion (75%) and selectivity (85%). This formulation outperformed the benchmark Au@TiO2, which achieved a similar conversion rate (80%) but exhibited lower selectivity (55%).

Stabilizing BiVO4 Photoanode in Bicarbonate Electrolyte for Efficient Photoelectrocatalytic Alcohol Oxidation.

In order to expand the application of bismuth vanadate (BiVO4) to the field of photoelectrochemistry, researchers have explored the potential of BiVO4 in catalyzing or degrading organic substances, potentially presenting a green and eco-friendly solution. A study was conducted to investigate the impact of electrolytes on the photocatalysis of benzyl alcohol by BiVO4. The research discovered that, in an acetonitrile electrolyte (pH 9) with sodium bicarbonate, BiVO4 catalyzed benzyl alcohol by introducing saturated V5+. This innovation addressed the issue of benzyl alcohol being susceptible to catalysis in an alkaline setting, as V5+ was prone to dissolution in pH 9 on BiVO4. The concern of the photocorrosion of BiVO4 was mitigated through two approaches. Firstly, the incorporation of a non-aqueous medium inhibited the formation of active material intermediates, reducing the susceptibility of the electrode surface to photocorrosion. Secondly, the presence of saturated V5+ further deterred the leaching of V5+. Concurrently, the production of carbonate radicals by bicarbonate played a vital role in catalyzing benzyl alcohol. The results show that, in this system, BiVO4 has the potential to oxidize benzyl alcohol by photocatalysis.

Regulation of Catalyst Immediate Environment Enables Acidic Electrochemical Benzyl Alcohol Oxidation to Benzaldehyde.

Electrocatalytic alcohol oxidation in acid offers a promising alternative to the kinetically sluggish water oxidation reaction toward low-energy H2 generation. However, electrocatalysts driving active and selective acidic alcohol electrochemical transformation are still scarce. In this work, we demonstrate efficient alcohol-to-aldehyde conversion achieved by reticular chemistry-based modification of the catalyst's immediate environment. Specifically, coating a Bi-based electrocatalyst with a thin layer of metal-organic framework (MOF) substantially improves its performance toward benzyl alcohol electro-oxidation to benzaldehyde in a 0.1 M H2SO4 electrolyte. Detailed analysis reveals that the MOF adlayer influences catalysis by increasing the reactivity of surface hydroxides as well as weakening the catalyst-benzaldehyde binding strength. In turn, low-potential (0.65 V) cathodic H2 evolution was obtained through coupling it with anodic benzyl alcohol electro-oxidation. Consequently, the presented approach could be implemented in a wide range of electrocatalytic oxidation reactions for energy-conversion application.

A binary dumbbell visible light driven photocatalyst for simultaneous hydrogen production with the selective oxidation of benzyl alcohol to benzaldehyde

Photocatalytic H2 production with selective oxidation of organic moieties in an aqueous medium is a fascinating research area. However, the rational design of photocatalysts and their photocatalytic performance are still inadequate. In this work, we efficiently synthesized the MoS2 tipped CdS nanowires (NWs) photocatalyst using soft templates via the two-step hydrothermal method for efficient H2 production with selective oxidation of benzyl alcohol (BO) under visible light illumination. The optimized MoS2 tipped CdS NWs (20 % MoS2) photocatalyst exhibits the highest photocatalytic H2 production efficiency of 13.55 mmol g−1 h−1 with 99 % selective oxidation of BO, which was 42.34 and 2.21 times greater photocatalytic performance than that of pristine CdS NWs and MoS2/CdS NWs, respectively. The directional loading of MoS2 at the tips of CdS NWs (as compared to nondirectional MoS2 at CdS NWs) is the key factor towards superior H2 production with 99 % selective oxidation of BO and has an inhibitory effect on the photo corrosion of pristine CdS NWs. Therefore, the amazing enhancement in the photocatalytic performance and selectivity of optimized MoS2 tipped CdS NWs (20 % MoS2) photocatalyst is due to the spatial separation of their photoexcited charge carriers through the Schottky junction. Moreover, the unique structure of the MoS2 flower at the tip of 1D CdS NWs offers separate active sites for adsorption and surface reactions such as H2 production at the MoS2 flower (confirmed by Pt photo deposition) and subsequently the selective oxidation of BO at the stem of CdS NWs. This rational design of a photocatalyst could be an inspiring work for the further development of an efficient photocatalytic system for H2 production with selective oxidation of BO (a strategy of mashing two potatoes with one fork).

Preparation of cobalt catalyst supported on perovskite-type oxide and application in liquid-phase selective oxidation reaction

Abstract Cobalt catalyst supported on the perovskite-type oxide sodium tantalate, NaTaO3 (NTO) was prepared by using the hydrothermal method and used in liquid-phase p-xylene oxidation, which led to p-methyl benzyl alcohol, p-tolualdehyde, and p-toluic acid. Investigation showed that the formation of alcohol and aldehyde was a competitive reaction. Further oxidation of the alcohol did not occur. On the other hand, the oxidation of p-tolualdehyde led to the formation of acid. Co-NTO catalyst showed higher selectivity toward the route of p-tolualdehyde than the p-methylbenzyl alcohol compared with the bulk Co3O4.

Novel half-sandwich ruthenium(II) nicotinic hydrazone complexes: An efficient class of catalyst for the N-alkylation of amines with benzyl alcohol via transfer hydrogen mechanism and effective antibacterial agents

A new series of half sandwich ruthenium(II) complexes supported by nicotinic acid hydrazone derivatives of general formula [Ru(ɳ6-p-cymene)(Cl)(L)], where L represents N’-benzylidenenicotinohydrazide (HL1), N’-(naphthalen-1-ylmethylene)nicotinohydrazide (HL2) or N’-(pyren-1-ylmethylene)nicotinohydrazide (HL3) were synthesized and fully characterized. The solid-state molecular structures of ligands and complexes were elucidated with single-crystal X-ray diffraction. The ligands HL1 and HL2 possess monoclinic crystal system with P21/c and C2/c space groups respectively, whereas all the three Ru(II) complexes C1–3 are typical three-legged piano-stool geometries with orthorhombic(Aba2) (C1) and triclinic(P-1) (C2–3) systems respectively. The catalytic activities of these ruthenium complexes in the synthesis of N-alkylated amines were explored. Under optimal reaction condition, the complex C3 was found to be the most efficient catalyst for the N-alkylation of primary to secondary amines using benzyl alcohol. A wide range of substrates have been studied that includes anilines bearing electron withdrawing/electron donating group, fused aromatic, heteroaromatic, alicyclic and aliphatic amines with good to excellent yield. In addition, the antibacterial activity of the complexes were tested against different human pathogenic bacteria, among them C2 complex with naphthyl moiety was found to be the most active one against both Gram-positive (S. aureus and E. faecalis) and Gram-negative (E. coli and K. pneumoniae) bacteria. These two different studies demonstrate the catalytic and biological importance of our newly prepared Ruthenium complex.

Oxygen vacancy engineering via doping Sr at the La-site of LaMnO3 to promote the ability for aerobic oxidation of benzyl alcohol

Aerobic selective oxidation is a prospective route to synthesize fine chemicals and their intermediates in modern industries, yet the development of an efficient catalyst remains a challenge, due to the limitations in O2 adsorption and activation. Herein, we report a promising La1-xSrxMnO3 (LSMO-x) perovskite oxide for aerobic oxidation of benzyl alcohol (BzOH) to benzaldehyde (BzH) via oxygen vacancy engineering. Through the substitution of Sr at the La-site of LaMnO3, the quantity of oxygen vacancies, which are active site of molecular oxygen, is greatly increased, thereby improving the efficiency for oxygen activation and the reaction activity. The optimal catalyst, LSMO-0.15, shows BzOH conversion of 97.0 % and BzH selectivity of 93.4 %, at 50 °C, for 3 h. The importance of oxygen vacancy for the reaction is verified by DFT calculations, by comparing the adsorption energies of reactants on LaMnO3 containing with and without oxygen vacancy. A reaction mechanism is also proposed, in which the adsorption and activation of O2 occurs on the oxygen vacancy, and that of BzOH occurs on the Mn4+ ions. The activated O2 and BzOH then react with each other to release H2O and yield BzH.

Modification of red mud catalyst using oxalic acid-assisted UV treatment for toluene removal

An innovative simplified modification method for red mud had been proposed, which enabled its utilization as an active Fe2O3-rich component for catalytic oxidation of toluene. The Box-Behnken design, based on Response Surface Methodology (RSM), was employed to optimize the modification of bauxite residue using oxalic acid combined with UV irradiation. Based on the experimental conditions, the optimal conditions for three independent parameters were determined: acid leaching time (2 hours), UV irradiation time (1 hour), and acid dosage (150 ml),which was in order to enhance the maximum catalytic efficiency of toluene at 300 °C. Under the optimal preparation conditions provided by the Box-Behnken design, the catalytic efficiency of toluene at 300°C could reach 99.2%. In comparison to the acid-modified mud (MRM) and untreated bauxite residue (RM), the aluminum refinery residue modified with oxalic acid-assisted UV irradiation (MRM-UV) exhibited the formation of oxalate sub-iron precipitates, resulting in significantly lower catalytic temperatures (238°C). Furthermore, through XRF, XRD, XPS, O2-TPD, and H2-TPD analysis, it was discovered that a large amount of iron oxide and calcium oxide formed CaO+Fe2O3→Ca2Fe2O5, strengthening the interaction between iron and calcium, augmenting the migration rate of lattice oxygen from the bulk phase to the surface. Consequently, T50 were reduced by 20.9% and 31.8% when compared to MRM and RM. Moreover, the CO2 selectivity of MRM-UV increased from 8.6% to 70.5% compared to RM at 300°C. Using in situ DRIFTS, the reaction pathway of toluene on MRM-UV was identified as benzyl alcohol → benzaldehyde or benzoyl → benzoate→maleic anhydride→CO2 and H2O. The process refinement reduced VOCs emissions and promoted sustainable waste management by combining oxalic acid with catalytically active red mud.

Macroporous NiFe-LDH accelerating highly-selective electrosynthesis of benzaldehyde accompanied with hydrogen production

Alkaline overall water splitting (OWS) is a potential technology for hydrogen (H2) production, however, the sluggish oxygen evolution reaction (OER) with high overpotential has limited its large-scale application. Herein, we successfully prepared the macroporous NiFe layered hydroxide (M-NiFe-LDH) on self-supported carbon cloth (CC) as electrocatalyst to drive an energy-saving device for both H2 production and benzyl alcohol (BA) oxidation to synthesize benzaldehyde (BAD). By utilizing the polystyrene (PS) microsphere templates and electrodeposition technology, CC@M-NiFe-LDH can be easily obtained after removing the PS templates. Due to the synergistic effect of bimetallic NiFe-LDH and macropores arrays which can expose more catalytic active sites, CC@M-NiFe-LDH electrocatalyst only needs a low potential of 1.31 VRHE to reach the current density of 10 mA cm−2 with a high BAD selectivity (∼99 %). Consequently, an energy-saving two-electrode device with both BAD electrosynthesis and H2 production can be assembled, which needs a low cell voltage of 1.648 V and electricity consumption of 3.60 kW h per cubic meter of H2, lower than that of OWS (1.826 V and 3.99 kW h).

Influence of the oxidic support material on the platinum-catalyzed benzyl alcohol oxidation

Influence of the oxidic support material on the platinum-catalyzed benzyl alcohol oxidation

Variation in the Floral Scent Chemistry of Nymphaea 'Eldorado', a Valuable Water Lily, with Different Flowering Stages and Flower Parts.

Nymphaea 'Eldorado', a valuable water lily, is a well-known fragrant plant in China. Studying the temporal and spatial characteristics of the floral components of this plant can provide a reference for the further development and utilization of water lily germplasm resources. In this study, headspace solid-phase microextraction (HS-SPME) combined with gas chromatography-mass spectrometry (GC-MS) was used to explore the types and relative contents of floral components at different flowering stages (S1: bud stage; S2: initial-flowering stage; S3: full-flowering stage; S4: end-flowering stage) and in different floral organs of N. 'Elidorado', combined with the observation of the microscopic structure of petals. A total of 60 volatile organic compounds (VOCs) were detected at different flowering stages, and there were significant differences in floral VOCs at different flowering stages and in different flower organs. The volatile compounds of N. 'Eldorado' can be divided into seven chemical classes,, namely, alkenes, alcohols, esters, aldehydes, ketones, alkanes, and others; the most common were alkenes and alkanes. A total of 39, 44, 47, and 42 volatile compounds were detected at S1, S2, S3, and S4. The VOCs present in high concentrations include benzaldehyde, benzyl alcohol, benzyl acetate, trans-α-bergamotene, α-curcumene, cis-α-farnesene, and so on. The types and total contents of volatiles at the full-flowering stage were higher than at other flowering stages. Comparing the VOCs in different parts of flower organs, it was found that the contents of alcohols, esters, and aldehydes were greatest in the petals, the alkenes in stamens were abundant with a relative content of up to 54.93%, and alkanes in the pistil were higher than in other parts. The types and total contents of volatiles in the stamens of N. 'Eldorado' were higher than those in other flower organs; they were the main part releasing fragrance. The observation of petal microstructure revealed that the size and quantity of the papillae on the epidermises of petals, the number of intracellular plastids, and the aggregates of floral components (osmophilic matrix granules) were significantly higher at the full-flowering stage than at the other flowering stages. This study suggested the main flowering stage and location at which the floral VOCs are released by N. 'Eldorado' and provided a reference for guiding the breeding of this water lily, exploring genetic patterns and developing related products.

An Experimental Study on Direct Hydroxylation of Toluene in a Dielectric Barrier Discharge System Under Ambient Conditions

ABSTRACT Non-thermal plasma is a promising alternative to be utilized for the synthesis of hydroxytoluenes through one-pot hydroxylation of toluene. Direct preparation of hydroxytoluenes from vaporized toluene was conducted in air at room temperature and atmospheric pressure using a dielectric-barrier discharge (DBD) reactor. The preliminary results obtained from this study showed that cresols were formed along with benzaldehyde, benzyl alcohol, and phenol. O atoms generated by air plasma in collision with toluene produced OH and benzyl radicals, which led to further reactions. The mechanism of the reaction of reactive oxygen species (ROS) with toluene and toluene-derived radicals to yield the observed oxidation products was discussed.

Forensic Evaluation of Ink Age by Raman Spectroscopy and Gas Chromatography-Mass Spectrometry (GC-MS)

Ink age analysis is a hot but challenging topic in the practice of document inspection and identification in forensic sciences. Due to the influence of ink components, paper, and storage environment on the aging process, strict validation of laboratory methods is required. In this study, Raman spectroscopy was investigated to determine ink age by analyzing the peak intensity of carbon black in neutral signature pens and has been recently used as evidence in legal documents. Through statistical analysis of Raman peak heights of inks naturally aged from 3 days to 18 months, the results demonstrate this approach is unsuitable for forensic purposes. Hence, appraisal conclusions should also be rejected by the procuratorate in actual cases. In order to further explore the identification of ink age, the volatilization rates of cyclohexanone, 1-butanol, propylene glycol, ethylene glycol, benzyl alcohol, diethylene glycol, glycerol, phenoxyethanol, and triethylene glycol commonly used in pens as a function of time were investigated. The results show that gas chromatography-mass spectrometry (GC-MS) is reliable to characterize the volatilization of these alcohols in documents. The residual levels of characteristic solvents (triethylene glycol in two samples and diethylene glycol in one) decreased significantly within 6 months and may be used to evaluate the ink age in documents.

Kinetic implications of (hierarchical) zeolite fouling during liquid-phase aromatics upgrading

The kinetics of fouling in large pore zeolites (BEA, MOR), including those with hierarchical pore systems, were probed during the Brønsted acid catalyzed reaction of benzyl alcohol (BA) with 1,3,5-trimethylbenzene (TMB) by varying reactant driving force (i.e., [TMB]0/[BA]0; 11–119). In BEA, initial deactivation rate constants (kD,0) decreased exponentially with [TMB]0/[BA]0, highlighting the significance of oxygenates as deactivation precursors. Further, seeding pores with oxygenates completely suppressed measured rates in parent MOR and BEA, while seeding with TMB had no effect. Comparisons of mass accumulations of different organics (low molecular weight reaction species and coke) as functions of ln([TMB]0/[BA]0) revealed that coke (derived from oxygenate-seeded polyalkylation of TMB) disproportionately controlled deactivation rates by damping apparent (diffusion-controlled) and intrinsic (diffusion-corrected) rate constants through proton losses and/or altered molecule confinement within shrinking pores. These kinetic consequences were delayed upon introduction of mesopores, demonstrating how zeolite porosity impacts coke proliferation and behavior in liquid-phase reactions.

Nanoplatelet Mordenite Zeolite with a Controlled Aspect Ratio: Implications for the Alkylation of Benzene with Benzyl Alcohol

Nanoplatelet Mordenite Zeolite with a Controlled Aspect Ratio: Implications for the Alkylation of Benzene with Benzyl Alcohol

Thermodynamic property estimations for aqueous primary, secondary, and tertiary alkylamines, benzylamines, and their corresponding aminiums across temperature and pressure are validated by measurements from experiments

On Earth and beyond, organic chemistry often occurs in the presence of water within environments that deviate drastically from ambient conditions (25 °C and 1 bar). Accurately predicting aqueous organic reaction pathways is crucial toward understanding planetary scale processes such as the cycling of elements crucial for life (e.g., carbon and nitrogen). Advanced thermodynamic modeling can be utilized to determine the favorability of various organic reactions based on geologically relevant ranges of temperature and pressure, as well as compositional variables (e.g., pH). However, data that would otherwise allow for a diversity of organic compounds and environmental conditions to be modeled are sparse and rarely tested with experiments, particularly with regard to organic-nitrogen compounds. In this work, we develop a framework to estimate thermodynamic properties at ambient conditions that can then be extrapolated across ranges of temperature and pressure for aqueous primary, secondary, and tertiary amines and aminiums (protonated amines), specifically those structures containing linear alkyl chains and benzyl functional groups. We also performed hydrothermal experiments (250 °C, ∼40 bar) involving reactions of methylamines to test our resulting thermodynamic models, and we compare our models for other alkylamines and benzylamines to previous empirical measurements from the literature. Specifically, we use existing thermodynamic data along with our estimates at ambient conditions in combination with a variety of existing extrapolation methods related to the revised Helgeson-Kirkham-Flowers (HKF) equations of state to generate temperature- and pressure-dependent predictions of acid dissociation constants (i.e., pKa values) that strongly agree with previous empirical measurements. We use similar methods to predict product distributions for reactions involving primary, secondary, and tertiary amines/aminiums, as well as ammonia/ammonium and corresponding alcohols whose collective distributions depend on reversible substitution reactions. Our predictions are in good agreement with our experimental results involving the methylamine reaction system as well as previous experiments involving the benzylamine reaction system, for which we also produced thermodynamic estimates involving benzyl alcohol. The agreement between independent theoretical predictions and experimental measurements suggests that our estimated properties can be applied to modeling amine chemistry in other experimental and natural aqueous systems that range in temperature and pressure, providing new tools for planetary exploration.