Effect of different substituent on the ESIPT process and fluorescence features of 2-(2-hydroxyphenyl)benzoxazole derivatives: A DFT/TD-DFT study.

In this contribution, four derivatives of 5'-(para-R-Phenylene) vinyl-2-(2'-hydroxyphenyl) benzoxazole (PVHBO) were ingeniously designed by introducing two electron-withdrawing substituents and two electron-donating substituents, aiming to investigate the influence of different substituents on the photophysical properties of PVHBO and the excited state intramolecular proton transfer (ESIPT) process via the density functional theory (DFT) and time-dependent DFT (TD-DFT) methods. By utilizing the geometric parameters and the simulated infrared (IR) spectra, we compared the intramolecular hydrogen bonds (IHBs) strengths in the S0 and S1 states of the molecules. Via conducting the hole-electron analysis, the reduction in fluorescence intensity for the enol and keto forms of PVHBO, PVHBO-MeO, and PVHBO-NH2 were also well explicated. Besides, the potential energy curves (PECs) and corresponding transition state (TS) structures for both S0 and S1 states were also constructed to accurately obtain energy barriers of forward and reversed proton transfer processes. The calculated absorption and fluorescence spectra also show that PVHBO-NH2 has the largest Stokes shifts of 158 nm and 219 nm in both the enol and keto states, with a significant increase in fluorescence intensity observed upon the induction of electron-withdrawing groups. Through this work, it can provide the theoretical basis for the design of novel luminescent materials.

Potential threats of microplastics and pathogenic bacteria to the immune system of the mussels Mytilus galloprovincialis.

As one of the main components of marine pollution, microplastics (MPs) inevitably enter the mussel aquaculture environment. At the same time, pathogenic bacteria, especially pathogens such as Vibrio, can cause illness outbreaks, leading to large-scale death of mussels. The potential harm of MPs and pathogenic bacteria to bivalve remains unclear. This study designed two experiments (1) mussels (Mytilus galloprovincialis) were exposed to 100 particles/L or 1,000 particles/L polymethyl methacrylate (PMMA, 17.01 ± 6.74 µm) MPs and 1 × 107 CFU/mL Vibrio parahaemolyticus at the same time (14 days), and (2) mussels were exposed to 100 particles/L or 1,000 particles/L MPs for a long time (30 days) and then exposed to 1 × 107 CFU/mL V. parahaemolyticus to explore the effects of these two stresses on the mussel immune system. The results showed that after the combined exposure of V. parahaemolyticus and MPs, the lysosomal membrane stability of hemocytes decreased, lysozyme activity was inhibited, and hemocytes were induced to produce more lectins and defensins to fight pathogenic invasion. Long-term exposure to MPs caused a large amount of energy consumption in mussels, inhibited most of the functions of humoral immunity, increased the risk of mussel infection with pathogenic bacteria, and negatively affected mussel condition factor, the number of hemocytes, and the number of byssuses. Mussels may allocate more energy to deal with MPs and pathogenic bacterial infections rather than for growth. Above all, MPs exposure can affect mussel immune function or reduce its stress resistance, which in turn has an impact on mollusk farming.

Effect of external electric fields on the ESDPT process and photophysical properties of 1,8-dihydroxy-2-naphthaldehyde.

In this work, by capitalizing on the density functional theory (DFT) and the time-dependent density functional theory (TD-DFT) methods, it has been systematically studied that the excited state double intramolecular proton transfer (ESDPT) process and the photophysical properties of 1,8-dihydroxy-2-naphthaldehyde (DHNA) are affected by the distinct external electric fields (EEFs). The obtained intramolecular hydrogen bond (IHB) parameters containing bond lengths and angles, as well as infrared (IR) vibrational spectra demonstrate that IHB strength changes in the distinct EEFs. Moreover, not only do the potential energy surfaces (PESs) indicate that the ESDPT process of DHNA is stepwise, but also increasing the positive EEF results in a decrease in the energy barrier accordingly, while vice versa. The absorption and fluorescence spectra also undergo a corresponding red or blue shift in the EEF; for instance, when the EEF changes from +10 × 10-4 a.u. to +20 × 10-4 a.u., the fluorescence peak undergoes a blue shift from 602 nm to 513 nm in the keto2 form. In a nutshell, the ESDPT process of DHNA can be influenced by the EEF, which will serve as a reference in regulating and controlling proton transfer that causes luminescence.

The physiological response of the clam Ruditapes philippinarum and scallop Chlamys farreri to varied concentrations of microplastics exposure.

Microplastics (MPs) pollution's impact on the marine ecosystem is widely recognized. This study compared the effects of polyethylene (PE) and polyethylene terephthalate (PET) on two bivalve species, Ruditapes philippinarum (clam) and Chlamys farreri (scallop), at two particle concentrations (10 and 1000 µg/L). MPs were found in the digestive glands and gills of both species. Although clearance rates showed no significant changes, exposure to different MPs caused oxidative stress, energy disruption, and lipid metabolism disorders in both clam and scallop. Histopathological damage was observed in gills and digestive glands. IBR values indicated increasing toxicity with concentration, with PET being more toxic than PE. WOE model suggested increasing hazard with concentration, highlighting higher PET toxicity on clam digestive glands. In contrast, PE hazard increased in gills, showing different species responses. R. philippinarum exhibited higher sensitivity to MPs than C. farreri, providing insights for assessing ecological risk under realistic conditions and stress conditions.

The pollution characteristics and risk assessment of microplastics in mollusks collected from the Bohai Sea.

Microplastics (MPs) pollution in the marine environment has become a global problem. In this study, a number of 21 mollusk species (n = 2006) with different feeding habits were collected from 11 sites along the Bohai Sea for MPs uptake analysis. The MPs in mollusk samples were isolated and identified by micro-Fourier Transform Infrared Spectroscopy (µ-FTIR), and an assessment of the health risks of MPs ingested by mollusk consumption is also conducted. Approximately 91.9 % of the individuals among all the collected species inhaled MPs, and there was an average abundance of 3.30 ± 2.04 items·individual-1 or 1.04 ± 0.74 items·g-1 of wet weight. The shape of MPs was mainly fiber, and a total number of 8 polymers were detected, of which rayon had the highest detection rate (58.3 %). The highest abundance, uptake rate and polymer composition of MPs was observed in creeping types, suggesting that they might ingest these MPs from their food. The gastropod Siphonalia subdilatata contains the highest levels of MPs, which may increase the risk of human exposure if consumed whole without removing the digestive gland. The polymer risk level of MPs in these mollusks was Level III (H = 299), presenting harmful MPs such as polyvinyl chloride. In terms of human exposure risk, the average risk of human exposure to MPs through consumption of Bohai mollusks is estimated to be 3399 items·(capita·year)-1 (424-9349 items·(capita·year)-1). Overall, this study provides a basis for the ecological and health Risk assessment of MPs in mollusks collected from the coastline of China.

Synchronous or stepwise Mechanism? a theoretical study on the Excited-State double proton transfer properties of shikonin and acetylshikosin.

The excited state double proton transfer (ESDPT) mechanism of shikonin (Shk) and its derivative acetylshikosin (AcShk) were studied by density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. The potential energy curves scanned along the coordinates of proton transfer indicate a preference for the ESDPT reaction to occur step by step. The AcShk molecule possesses an additional reaction pathway in comparison to the Shk molecule. Furthermore, efforts have been made to compute the absorption and fluorescence peak, which exhibits favorable conformity with the experimental findings of the system investigated. The fluorescence spectra in cyclohexane and acetonitrile solvents indicate that the solvent polarity affects the location of the ESDPT fluorescence peak in both Shk and AcShk systems. The fluorescence spectra concentrated in the green light region (504 nm âˆ¼ 550 nm) are obtained, which has the potential to promote human health through disinfection and boosting the immune system.

Alteration of microbial mediated carbon cycle and antibiotic resistance genes during plastisphere formation in coastal area.

Microorganisms can attach on the surface of microplastics (MPs) through biological fouling process to form a diverse community called the "plastisphere", which has attracted extensive attention. Although the microbial structure and composition of biofilm have been studied, the knowledge of its microbial function and ecological risk is still limited. In this study, we investigated how the surface properties of MPs affect the biofilm communities and metabolic features under different environmental conditions, and explored the biofilm enrichment of antibiotic resistance genes (ARGs). The results showed that the incubation time, habitat and MPs aging state significantly influenced the structure and composition of biofilm microbial communities, and a small amount of pathogens have been found in the MPs-attached biofilm. The microbial carbon utilization capacity of the biofilm in different incubation habitats varies greatly with highest metabolism capacity appear in the river. The utilization efficiency of different carbon sources is polymer > carbohydrate > amino acid > carboxylic acids > amine/amide, which indicates that the biofilm communities have selectivity between different types of carbon sources. More importantly, ARGs were detected in all the MPs samples and showed a trend of estuary > river > marine. The aged MPs can accumulate more ARGs than the virgin items. In general, MPs in the aquatic environment may become a carrier for pathogens and ARGs to spread to other environment, which may enhance their potential risks to the ecosystem and human health.

Microfluidic fabrication of size-controlled nanocarriers with improved stability and biocompatibility for astaxanthin delivery.

Improving the stability of astaxanthin (AST) is a vital way to enhance its oral bioavailability. In this study, a microfluidic strategy for the preparation of astaxanthin nano-encapsulation system was proposed. Thanks to the precise control of microfluidic and the rapid preparation ability of the Mannich reaction, the resulting astaxanthin nano-encapsulation system (AST-ACNs-NPs) was obtained with average sizes of 200 nm, uniform spherical shape and high encapsulation rate of 75%. AST was successfully doped into the nanocarriers, according to the findings of the DFT calculation, fluorescence spectrum, Fourier transform spectroscopy, and UV-vis absorption spectroscopy. Compared with free AST, AST-ACNs-NPs showed better stability under the conditions of high temperature, pH and UV light with<20% activity loss rate. The nano-encapsulation system containing AST could significantly reduce the hydrogen peroxide produced by reactive oxygen species, keep the potential of the mitochondrial membrane at a healthy level, and improve the antioxidant ability of H2O2-induced RAW 264.7 cells. These results indicated that microfluidics-based astaxanthin delivery system is an effective solution to improve the bioaccessibility of bioactive substances and has potential application value in food industry.

Regulating the photophysical properties of ESIPT-based fluorescent probes by functional group substitution: a DFT/TDDFT study.

CONTEXT: In recent years, fluorescent probe technology has received more and more attention. However, the photophysical and photochemical properties of probe molecules still need to be further explored. This paper presents the excited state intramolecular proton transfer (ESIPT) processes and photophysical properties of the probe molecule 4-bromo-2-((E)-((Z)-((5-bromo-1H-indol-2-yl) methylene) hydrazono) methyl) phenol (BHPL) and its four derivatives (BHPL2, BHPL3, BHPL4, and BHPL5). Infrared spectra and geometric structure analyses revealed that introducing the -NH2 group on the benzene ring with the hydroxyl group will enhance the intramolecular hydrogen bond, which benefits the ESIPT process. Combining their absorption and fluorescence spectra, it can be concluded that BHPL2 and BHPL4 are both excellent probe candidates due to their large Stokes shift. The hole and electron and root mean square displacement analyses manifest that the fluorescence quenching of BHPL4 may be due to the intramolecular charge transfer process. Potential energy curves of BHPL and its four derivatives noted that ESIPT process of the BHPL2 is the most favorable to occur. The frontier molecular orbital and NBO analyses indicated that besides introducing electron-donating groups to reduce the energy gap and enhance fluorescence emission, introducing double electron-withdrawing groups can also achieve this effect, explaining why the energy barrier of ESIPT process for BHPL2 is lower than BHPL5. This work would provide the theoretical basis for designing novel fluorescence probes with more prominent properties. METHODS: The ground (S0) and excited (S1) state structures of all compounds were optimized by density functional theory (DFT) and time-dependent (TDDFT) method, with B3LYP/6-311+G(d,p) level, respectively. The infrared spectra and potential energy curves were simulated at the same theoretical level. The reduced density gradient scatter plots and interaction region indicator isosurfaces were drawn using Multiwfn and VMD programs. The absorption and fluorescence spectra were simulated by the TDDFT/B3PW91/6-311+G(d,p) method. All the calculations in this work are carried out in Gaussian 16 program package.

The adverse impact of microplastics and their attached pathogen on hemocyte function and antioxidative response in the mussel Mytilus galloprovincialis.

Microplastics (MPs) are widely distributed in marine environments, and they are easily attached by various microorganisms, including pathogenic bacteria. When bivalves mistakenly eat MPs, pathogenic bacteria attached to MPs enter their bodies through the Trojan horse effect, causing adverse effects. In this study, the mussel Mytilus galloprovincialis was exposed to aged polymethylmethacrylate MPs (PMMA-MPs, 20 µm) and Vibrio parahaemolyticus attached to PMMA-MPs to explore the effect of synergistic exposure by measuring lysosomal membrane stability, ROS content, phagocytosis, apoptosis in hemocytes, antioxidative enzyme activities and apoptosis-related gene expression in gills and digestive glands. The results showed that MP exposure alone did not cause significant oxidative stress in mussels, but after long-term coexposure to MPs and V. parahaemolyticus, the activities of antioxidant enzymes were significantly inhibited in the gills of mussels. Both single MP exposure and coexposure will affect hemocyte function. Coexposure can induce hemocytes to produce higher ROS, improve phagocytosis, significantly reduce the stability of the lysosome membrane, and induce the expression of apoptosis-related genes, causing apoptosis of hemocytes compared with single MP exposure. Our results demonstrate that MPs attached to pathogenic bacteria have stronger toxic effects on mussels, which also suggests that MPs with pathogenic bacteria might have an influence on the immune system and cause disease in mollusks. Thus, MPs may mediate the transmission of pathogens in marine environments, posing a threat to marine animals and human health. This study provides a scientific basis for the ecological risk assessment of MP pollution in marine environments.

The evaluation of lateral incisor adjacent to treated labial inversely impacted maxillary central incisor: A retrospective follow-up study.

INTRODUCTION: This retrospective study aimed to evaluate the further development of the lateral incisor and its associated periodontium adjacent to the treated labial inversely impacted maxillary central incisor. METHODS: We enrolled 23 participants (average age, 8.24 ± 1.43 years) undergoing a mean follow-up period of 31.10 ± 13.05 months. Each participant had an unimpacted lateral incisor and a successfully treated unilateral labial inversely impacted maxillary central incisor. The contralateral lateral incisors served as controls. Cone-beam computed tomography data were available for treatment completion and follow-up stages. The variables (including root length, dental age, root canal width, root-crown angulation, and alveolar bone loss and thickness) were evaluated with Dolphin Imaging software (version 11.95; Dolphin Imaging and Management Solutions, Chatsworth, Calif). RESULTS: At the follow-up stage, the lateral incisors in the impacted side had significantly longer root lengths, smaller root canal widths, and thinner labial bone widths at the apex than at the posttreatment stage (P <0.001, P = 0.036, and P = 0.001, respectively). A significant lateral incisor root length reduction was noted when comparing the impacted and contralateral sides, although no variation was observed in root canal width. Similarly, crown-root angulation of the lateral incisor on the impacted side was significantly larger than that of the contralateral lateral incisor. The lateral incisor on the impacted side also had thicker labial and thinner lingual bone widths at the apex than the contralateral lateral incisor. CONCLUSIONS: The lateral incisor adjacent to the successfully treated labial inversely impacted maxillary central incisor showed continuous growth during follow-up stages, exhibiting a similar morphology and alveolar bone quality but shorter root length, larger root angulation, and thinner lingual bone width at the apex than those of the contralateral lateral incisors.

First record of microplastics in the Gigantidas platifrons (Mytilidae: Bathymodiolus) and Shinkaia crosnieri (Munidopsidae: Shinkaia) from cold-seep in the South China Sea.

The deep sea is considered the final sink for microplastics (MPs) pollution in marine environments. Despite MPs being consumed by many organisms, their presence in cold-seep organisms remains unclear. At cold seep site F in the South China Sea, which lies 1155 m deep, MPs were investigated in Gigantidas platifrons and Shinkaia crosnieri, both ecologically important species. Microplastics ingestion rates were 80.98 % and 81.25 % in G. platifrons and S. crosnieri, respectively. The average MPs abundance for G. platifrons and S. crosnieri was 2.80 ± 0.69 MPs/ind (2.20 ± 2.75 MPs/g) and 2.30 ± 0.27 MPs/ind (4.74 ± 3.08 MPs/g), with no significant difference between species. There were predominantly fibrous MPs ingested by cold-seep organisms, sized 500-1000 µm, blue in color, and polyethylene terephthalate and cellophane in composition. The results confirm the presence of MPs in cold-seep organisms in the South China Sea, providing further evidence that MP pollution exists in the deep sea.

Theoretically unveiling the effect of solvent polarities on ESDPT mechanisms and photophysical properties of hydroxyanthraquinones.

In this work, we were devoted to explore the effect of solvent polarities on the excited-state intramolecular proton transfer (ESIPT) process of 1-acetamido-4-hydroxyanthraquinone (AcHAQ) in three different polarity solvents (acetonitrile, chloroform, and cyclohexane) based on the density functional theory (DFT) and time-dependent DFT (TD-DFT) methods, and thereby regulating the distribution ratio between the dual excited-state isomers (enol and keto). The calculated geometrical parameters and infrared (IR) vibrational spectra have confirmed the excited-state intramolecular hydrogen bond (IHB) strengthening mechanism. Natural bond orbital (NBO) population analysis indicates that the intramolecular charge transfer (ICT) around IHBs has enhanced IHB, thereby triggering the ESIPT reaction. In addition, results obtained from the scanned potential energy curve (PEC) manifest that ESIPT process prefers to occur along the O3-H2…O1 IHB and energy barriers corresponding to the proton transfer in ACN are the lowest among all the studied solvents.

Toxicokinetics and toxicodynamics of plastic and metallic nanoparticles: A comparative study in shrimp.

Nanoplastic is recognized as an emerging environmental pollutant due to the anticipated ubiquitous distribution, increasing concentration in the ocean, and potential adverse health effects. While our understanding of the ecological impacts of nanoplastics is still limited, we benefit from relatively rich toxicological studies on other nanoparticles such as nano metal oxides. However, the similarity and difference in the toxicokinetic and toxicodynamic aspects of plastic and metallic nanoparticles remain largely unknown. In this study, juvenile Pacific white shrimp Litopenaeus vannamei was exposed to two types of nanoparticles at environmentally relative low and high concentrations, i.e., 100 nm polystyrene nanoplastics (nano-PS) and titanium dioxide nanoparticles (nano-TiO2) via dietary exposure for 28 days. The systematic toxicological evaluation aimed to quantitatively compare the accumulation, excretion, and toxic effects of nano-PS and nano-TiO2. Our results demonstrated that both nanoparticles were ingested by L. vannamei with lower egestion of nano-TiO2 than nano-PS. Both nanoparticles inhibited the growth of shrimps, damaged tissue structures of the intestine and hepatopancreas, disrupted expression of immune-related genes, and induced intestinal microbiota dysbiosis. Nano-PS exposure caused proliferative cells in the intestinal tissue, and the disturbance to the intestinal microbes was also more serious than that of nano-TiO2. The results indicated that the effect of nano-PS on the intestinal tissue of L. vannamei was more severe than that of nano-TiO2 with the same particle size. The study provides new theoretical basis of the similarity and differences of their toxicity, and highlights the current lack of knowledge on various aspects of absorption, distribution, metabolism, and excretion (ADME) pathways of nanoplastics.

Insights into the photophysical properties of 2-(2'-hydroxyphenyl) benzazoles derivatives: Application of ESIPT mechanism on UV absorbers.

In this present work, four novel molecules (BPN, BPNS, BPS, and BPSN), possessing excited-state intramolecular proton transfer (ESIPT) characteristics, were designed to quantify the impacts of substituent effects on their photophysical properties. By exploring the primary geometrical parameters concerning hydrogen bonds, it should be noticed that the intramolecular hydrogen bonds (IHBs) of the studied molecules have been strengthened at S1 state. Infrared vibrational spectra analysis illustrates that adding electron-donating group thiophene to the proton donor side can weaken the IHBs in comparison to the electron-withdrawing group pyridine. Through investigating the absorption and fluorescence spectra, it can be clearly found that the maximum absorption peaks of the studied molecules are all located in the UVA region, and their regions of fluorescence peaks are harmless to human skin. Furthermore, considering the light intensity factor, it can be concluded that BPNS is the most potential to be used as UV absorbers in the studied molecules. This work investigates the effects of the positions and types of substituent groups on photophysical properties of 2-(2'-hydroxyphenyl) benzazoles derivatives, which can help design and exploit novel UV absorbers.

Substituent derivatives of benzothiazole-based fluorescence probes for hydrazine with conspicuous luminescence properties: A theoretical study.

In the present work, four probe molecules for detecting hydrazine have been designed based on the 2-(4-Acetoxy-3-benzothiazole-2-yl-phenyl)-4-methyl-thiazole- 5-carboxylic acid ethyl ester (HP1) to investigate the influence of the amino and cyano groups on the excited-state intramolecular proton transfer (ESIPT) behavior and photophysical properties. The changes in hydrogen bond strength indicate that the intramolecular hydrogen bond of all probe products is enhanced upon photoexcitation. Frontier molecular orbitals (FMOs) and natural bond orbital (NBO) reveal the driving force of ESIPT. In addition, the potential energy curves and transition state theory explain the reason for the single fluorescence phenomenon in the experiment. The simulated absorption and fluorescence spectra of HP1 and its product (HPP1) are completely consistent with the experimental results, which also verify the viewpoint. Meanwhile the cyano derivative HPP4 exhibits a larger Stokes-shift (201 nm) than that of HPP1 (145 nm) and has the same low energy barrier as HPP1. These excellent properties allow HPP4 to be a fluorescent probe with superior performance than the original molecule. In conclusion, this work can provide a theoretical basis for the design and synthesis of more sensitive fluorescent probes for the detection of hydrazine.

Pd-Catalyzed Selective B(6)-H Phosphorization of nido-Carboranes via Cascade Deboronation/B-H Activation from closo-Carboranes.

Efficient Pd-catalyzed regioselective B(6)-H phosphorization of nido-carboranes via cascade deboronation/B-H activation of readily available C-substituted o-carboranes with various phosphines using 3-methylpyridine or isoquinoline as a directing group in combination with pyridine ligands has been developed, affording unprecedented B(6)-phosphinated nido-carborane derivatives with high selectivity in a simple one-pot process.

Theoretical study on the optical properties of an ESIPT-based fluorescent probe for phosgene.

A fluorescent probe Pi with the excited-state intramolecular proton transfer (ESIPT) properties was synthesized and used to detect the phosgene in solution and gas phases. However, the detection mechanism of the fluorescent probe needs to be further studied. Herein, the density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods were adopted to explore the molecular structures and electronic spectra properties of probe and its product Pio after reacting with phosgene. Through analysis for molecular structure parameters and infrared vibrations accompanied with the hydrogen bond of Pi, it is confirmed that the intramolecular hydrogen bond of Pi is enhanced under light excitation, which illustrates the occurrence of ESIPT reaction combined with the scanned potential energy curves. It can be seen from the simulated spectra that Pi shows double fluorescence through ESIPT process, while the fluorescent product Pio exhibits the single fluorescence due to the disappearance of intramolecular hydrogen bond. Through the study on the structure and optical properties of Pi and Pio, it can be helpful to deeply understand the intrinsic mechanism of the detection of phosgene by the Pi molecule probe, which also supplies a reference to the further study about the fluorescence probe.

Theoretical Study on the Atom-Substituted Quinazoline Derivatives with Faint Emission as Potential Sunscreens.

Two novel compounds (HQS and HQSe) with excited-state intramolecular proton transfer (ESIPT) properties were designed based on the compound 2-(2-hydroxy-3-ethoxyphenyl)-3H-quinazolin-4-one (HQ). The parameters related to the ESIPT properties and electronic spectra of HQ and its derivatives were calculated using density functional theory and time-dependent density functional theory methods. The obtained geometric configurations, infrared vibrational spectra, and reduced density gradient scatter plots have shown that the intramolecular hydrogen bond O1···H1-N1 has been weakened upon photoexcitation. Moreover, from the scanned potential energy curves, it can be found that the ESIPT processes of the three compounds have no energy barriers. It is noteworthy that HQS and HQSe can strongly absorb light in the UVA region (∼340 nm) and exhibit weak fluorescence emission in the visible light region, which comes from the keto configuration. The special optical properties of HQS and HQSe can promote their application as potential sunscreen agents.

A DFT study on the structure activity relationship of the natural xanthotoxin-based pharmaceutical cocrystals.

In this work, the pharmaceutical cocrystals xanthotoxin-para-aminobenzoic acid (XT-PABA) and xanthotoxin-oxalic acid (XT-OA) were systematically investigated in the gas and water phases by using the quantum chemical approach. The weak intermolecular interactions have been estimated and the O1…H4 (O1…H5) intermolecular hydrogen bond (IHB) with moderate intensity and partial covalent natures was confirmed based on the computed structural parameters, topology analysis, and reduced density gradient (RDG) isosurfaces. The electrophilic and nucleophilic reactivities of different positions associated with intermolecular interactions in XT, PABA, and OA were predicted by plotting the molecular electrostatic potential (MESP) diagrams. The calculated natural bond orbital (NBO) population analysis has quantitatively unveiled the intrinsic reason for the variations in weak intermolecular interactions within XT-PABA and XT-OA cocrystals, from the gas phase to the water phase. Besides, the frontier molecular orbitals (FMOs), Fukui function, and various global reactivity descriptors were computed to measure the chemical reactivity of all the investigated molecular systems. The XT-PABA and XT-OA cocrystals explored in this work could be regarded as valuable exemplar systems to design and synthesize the high-efficiency pharmaceutical cocrystals in the experiment.