Intermolecular H-bonding Interactions Research Articles

Nitrogen doped activated carbon derived from chitosan/hexamethylenetetramine: structural and CO2 adsorption properties

Chitosan and chitosan/hexamethylenetetramine (HMT) macrospheres were prepared respectively by dropping the solution of chitosan and chitosan/HMT (in wt/wt ratios of 1:1 and 1:3) in aq. NaOH solution. Here, HMT served as an additional nitrogen precursor for in situ N-doping with chitosan derived activated carbon (AC). The as-formed macrospheres were impregnated using ZnCl2, freeze-dried and carbonized at 500 °C under inert atmosphere to yield ACs of size ranging from 2.5 to 2.8 mm. All the samples were characterized using SEM, EDS, CHNS Analyzer, TGA, FT-IR, Raman, XRD and BET surface area analyzer. All the samples showed mesoporous characteristics. The surface area of the AC without HMT, with 1:1 HMT and 1:3 HMT were 391.502, 259.017 and 111.717 m2/g respectively. Similarly, the pore volumes of AC without HMT, with 1:1 HMT and 1:3 HMT were 0.138, 0.095 and 0.075 cc/g respectively. The chitosan/HMT derived AC possessed higher N-content and better thermal stability, however exhibited lower surface properties with increasing HMT content. The CO2 adsorption capacity of chitosan derived AC was 97.98 mg/g while that of AC with 1:1 HMT and 1:3 HMT were 72.95 mg/g, 55.11 mg/g respectively at 25 °C and 1 bar. Deterioration in adsorption capacity of chitosan/HMT derived AC may be attributed to the physical cross-linking of chitosan polymer chains induced by increase in pH with addition of HMT and also the intermolecular H-bonding interaction between HMT and chitosan, which in turn reduces the surface area of as-formed N-doped ACs progressively.

Expanding the Scope of Metastable Species in Hydrogen Bonding-Directed Supramolecular Polymerization.

We reveal unique hydrogen (H‐) bonding patterns and exploit them to control the kinetics, pathways and length of supramolecular polymers (SPs). New bisamide‐containing monomers were designed to elucidate the role of competing intra‐ vs. intermolecular H‐bonding interactions on the kinetics of supramolecular polymerization (SP). Remarkably, two polymerization‐inactive metastable states were discovered. Contrary to previous examples, the commonly assumed intramolecularly H‐bonded monomer does not evolve into intermolecularly H‐bonded SPs via ring opening, but rather forms a metastable dimer. In this dimer, all H‐bonding sites are saturated, either intra‐ or intermolecularly, hampering elongation. The dimers exhibit an advantageous preorganization, which upon opening of the intramolecular portion of the H‐bonding motif facilitates SP in a consecutive process. The retardation of spontaneous self‐assembly as a result of two metastable states enables length control in SP by seed‐mediated growth.

Synthesis and characterization of a tertiary amine:boric acid (1:1) co-crystal and a neutral zwitterionic diamine pentaboron adduct

The syntheses of the 4,4′-trimethylenebis(N-methylpiperidine):boric acid (1:1) co-crystal, 4,4′-(1-MeNC5H9)2(CH2)3.B(OH)3 (1), and a zwitterionic tetrahydroxidohexaoxidopentaboron adduct, [B5O6(OH)4(κN-NH2CH2CH2NHEt2).H2O (2), (NH2CH2CH2NEt2 = deen) from appropriate combinatorial libraries primed with B(OH)3, are reported together with their spectroscopic (NMR, IR) and single-crystal XRD characterization data. Solid-state H-bond interactions are the likely strong drivers for their formation, and these are described in detail. H-bond networks present in co-crystal 1 include C22(16), R22(8), and R66(36) whilst zwitterionic pentaboron derivative 2 has three R22(8) intermolecular H-bond interactions and the Et2NH- group is involved in a S(7) intramolecular H-bond. Thermal (TGA/DSC) data are also reported for 1 which thermally decomposes to B2O3, in a multistage process: dehydration (60–70 °C) and oxidation and further dehydration (90–700 °C).

Anin silicopredictive method to select multi-monomer combinations for peptide imprinting

In silico methods enable optimizing artificial receptors such that constructive mimics of natural antibodies can be envisaged. The introduction of combinatorial synthesis strategies via multi-monomer combinations has improved the performance of molecularly imprinted polymers (MIP) significantly. However, it remains experimentally challenging to screen thousands of combinations resulting from a large library of monomers. The present study introduces a molecular mechanics based multi-monomer simultaneous docking approach (MMSD) to computationally screen monomer combinations according to their potential, facilitating selective molecular imprints. Thereby, the diversity of multipoint interactions realizable with a peptide surface is efficiently explored yielding how individual monomer binding capacities constructively or adversely add up when docked together. Additionally, spatially distributed molecular models were mapped for analyzing intermolecular H-bonding and hydrophobic interactions resulting from single monomer docking, as well as bi- and tri-monomer simultaneous docking. A direct impact of complex formation on the binding capacity of the resulting MIPs has been observed. In a first small-scale study, the predictive potential of the MMSD approach was validated via experimentally applied polymer combinations for peptide imprinting via the scoring functions established during the screening process. MMSD clearly enables rational design of MIPs for synthesizing more sensitive and selective artificial receptor materials especially for peptide and protein-epitope templates.

Quantum Density Functional Theory Studies on Additive Hydration of Tuftsin Tetrapeptide

Density functional B3LYP method has been used to study the molecular properties of the tuftsin tetrapeptide (threonine‐lysine‐proline‐arginine) and its retro form (arginine‐proline‐lysine‐threonine). The influence of single water molecule on the conformations and relative stabilities of solvated tuftsin complexes has been studied by placing the water molecule at the individual amino acid residues of both the tuftsin complexes. The contribution of four water molecules to the system energetics of tuftsin complexes has also been analyzed. The conformational changes occurred in the solvated tuftsin complexes have been explored through their dihedral angles. The tuftsin is found to be sensitive to structural changes, and our results indicate that water‐tuftsin hydrogen bonds (H‐bonds), in addition to intramolecular H‐bonds, stabilize the β‐turn structure with H‐bonds between threonine and arginine residues of tuftsin. Difference in the stability of the hydrated complexes is confined to the amino acid residues at which the water molecule is attached to tuftsin. The interaction energy calculations have been used to investigate the strength of the intermolecular H‐bond interactions. The AIM theory and NBO analysis were employed to survey the H‐bonding patterns in hydrated tuftsin complexes. The maximum ellipticity value (0.129) is noted for the Cα‐H (Arg)…O (W) interaction in Tuftsin…4W complex which indicates the higher chance of structural deformation under external perturbations. The interactions between oxygen lone pairs in water and C‐H antibond orbitals of tuftsin and retro tuftsin complexes exist with E(2) in the range of 4.03‐5.7 and 3.59‐4.14 kcal/mol, respectively.

Structural Isomerization Effect on the Triplet Energy Consumption Process of Organic Room-Temperature Phosphorescence Molecules: A QM/MM Study

Organic room-temperature phosphorescence (RTP) materials with long lifetimes and high efficiency have attracted great attention in recent studies. Structural isomerism with ester substituents at different positions could intrinsically influence the luminescence efficiency and operational lifetime of RTP molecules. A theoretical study to reveal the intrinsic structure–property relationship is highly desired. Herein, based on density functional theory (DFT) and time-dependent density functional theory (TD-DFT), the geometric and electronic properties of three isomers (o-MCBA, m-MCBA, and p-MCBA proposed by Tang) are investigated. Furthermore, the Huang–Rhys factor and reorganization energy are analyzed, and exciton dynamic processes, such as the intersystem crossing (ISC) process and three decay channels for the energy consumption process of the first triplet excited state (T1) based on the thermal vibration correlation function (TVCF) method, are discussed in detail. The results show that intermolecular interactions can restrict the rotation motions of the dihedral angle and the vibration motions of the bond angle for o-MCBA and m-MCBA. In addition, decreased Huang–Rhys factor and reorganization energy are found and a hindered nonradiative consumption process is determined. For p-MCBA in the solid phase, the rotation motions are partly restricted by the solid-state effect and the vibration motions of the bond length are effectively promoted by intermolecular H-bond interactions. In addition, the spin–orbit coupling (SOC) effect is enhanced by the solid-state effect, which is helpful to facilitate the ISC process. Through this study, we pursue opportunities to detect the relationship between basic molecular structures and RTP properties, which could take advantage of the unique molecular design to develop high-performance emitting molecules.

Effect of chirality and redox potentials on the cytotoxicity of new ferrocene functionalized chiral tertiary amines

Optically pure enantiomeric pair viz. ferrocene functionalized chiral tertiary amines S,S-(-)-1 and R,R-(+)-2 have been synthesized from ferrocenylmethylamine to probe the influence of chirality and the redox potential on their anti-proliferative activity. Compounds were characterized by microanalysis, HPLC, 1H, 13C NMR, UV-visible, fluorescence, FTIR, thermogravimetric and crystallographic techniques. The single crystal X-ray diffraction (SCXRD) study revealed that the molecules of 1 holding S,S-chirality at benzylic carbons forms a fascinating M-helix while 2 holding R,R-chirality at benzylic carbons forms P-helix by involving intra- and intermolecular H-bonding interactions as verified by Hirshfeld surface analysis. Chirality-related influence was observed on the antiproliferative activity of enantiomeric pair and at the supramolecular level. For instance, enantiomer R,R-(+)-2 is found to be highly active against all the investigated human carcinoma cell lines MCF 7, IMR 32, HepG2, and immortal L132 cell lines. In particular, R,R-(+)-2 exhibited more than 10 folds better antiproliferation (IC 50: 6.35±0.19 μM) than other enantiomer S,S-(-)-1 (IC50: 65.96 ± 0.12 μM) and four folds better activity than highly successful anticancer drug, cisplatin (IC50: 24.3 ± 1.7 μM) against Hep G2 cell line. The electrochemical, DFT calculations and molecular docking study have been performed to justify the experimental outcomes.

Mechanistically understanding adsorption of methyl orange, indigo carmine, and methylene blue onto ionic/nonionic polystyrene adsorbents

The involved interaction information concerning adsorbate-adsorbate and adsorbate-adsorbent is indispensable for developing and optimizing adsorption treatment of dye wastewater. Single and bi-solute adsorption of methyl orange (MO), indigo carmine (IC), and methylene blue (MB) on polystyrene anion exchanger (PsAX), defunctionalized version of PsAX (DF-PsAX), and hyper-cross-linked polystyrene adsorbent (MN200) were investigated to obtain a mechanistic understanding. Under acidic condition, higher adsorption efficiencies of PsAX due to extra intermolecular interactions of MO between the protonated tertiary amine group and the sulfate groups were observed, while strong alkaline condition is favorable for the adsorption of IC and MB by PsAX. MN200 exhibited much larger adsorption capacity toward MB than that toward MO or IC, because the fused-rings structure of MB is more polarizable and can form stronger nonionic intermolecular attractions with the matrix structure of polystyrene adsorbents. Bi-solute adsorption reveals that MO has obvious competitive effect toward IC adsorption at low concentrations, but it is not the case for the adsorption at high concentrations, where IC molecules can form intermolecular H-bonding interactions to defend the competition. the thermodynamic parameters confirm the endothermic and spontaneous nature of MO adsorption by PsAX, and ≈ 48 KJ mol−1 of the enthalpy change (∆H) imply the adsorption is not just physical absorption. Additionally, water/ethanol mixture solution of NaCl can almost thoroughly regenerate the exhausted PsAX, whereas only aqueous solution without ethanol is invalid.

Bulk and Surface Conformations in Solid-State Lovastatin: Spectroscopic and Molecular Dynamics Studies

Conformational flexibility in molecules can give rise to a range of functional group terminations at crystal surfaces and dynamic disorder in the bulk. In this work, we explore the conformational behavior of the drug molecule lovastatin in the crystallographically disordered solid and at crystal surfaces through a combination of computational modeling and spectroscopy. Gas-phase and periodic quantum-chemical calculations are used to study the potential energy surface associated with rotatable bonds to examine the disorder in bulk. These calculations are combined with vibrational and X-ray photoelectron spectroscopy measurements to obtain insight into the conformations in bulk and at the surface. Our MD simulations show that the bulk disorder is driven by cooperative motion of the butyl group on the S-butanoate moiety along one crystallographic direction beyond a unit cell. The calculations show that the O-H group can rotate relatively freely between two low-energy conformers in the gas phase but is locked in position by intermolecular H-bonding interactions in the bulk crystal, and we find tentative spectroscopic evidence for the second conformer being present at the surface. We also comment on the relative utility of these different techniques for studying molecular conformation in bulk and at surfaces and highlight possible areas for future developments.

Looking for Minor Phenolic Compounds in Extra Virgin Olive Oils Using Neutron and Raman Spectroscopies.

Extra virgin olive oil (EVOO) is defined as a functional food as it contains numerous phenolic components with well-recognized health-beneficial properties, such as high antioxidant and anti-inflammatory capacity. These characteristics depend on their structural/conformational behavior, which is largely determined by intra- and intermolecular H-bond interactions. While the vibrational dynamics of isolated compounds have been studied in a number of recent investigations, their signal in a real-life sample of EVOO is overwhelmed by the major constituent acids. Here, we provide a full characterization of the vibrational spectroscopic signal from commercially available EVOO samples using Inelastic Neutron Scattering (INS) and Raman spectroscopies. The spectra are dominated by CH2 vibrations, especially at about 750 cm−1 and 1300 cm−1. By comparison with the spectra from hydroxytyrosol and other minor phenolic compounds, we show that the best regions in which to look for the structure–activity information related to the minor polar compounds is at 675 and 1200 cm−1 for hydroxytyrosol, and around 450 cm−1 for all minor polar compounds used as reference, especially if a selectively deuterated sample is available. The regional origin of the EVOO samples investigated appears to be related to the different amount of phenolic esters versus acids as reflected by the relative intensities of the peaks at 1655 and 1747 cm−1.

Metal-free synthesis and single crystal X-ray analysis of 4-aryl-6-hydroxy-2Η-pyran-2-cyanomethylenes

The synthesis of 4-aryl-2H-pyran-2-ones 7 was accomplished by rearrangement of 6-aryl-2H-pyran-ones 5 with ethyl cyanoacetate 6 in the presence of a base in DMF at room temperature. The reaction products were achieved in good yields. The reaction products were characterized by their spectroscopic analysis. The structure of compound 7a was confirmed by its single crystal X-ray analysis. Moreover, single crystal X-ray study of compound 7a showed rare plausible peri oxygen-oxygen interactions between O2 and O3. Further compound 7a showed homodimer intermolecular H-bonding interactions between nitrogen and OH groups along with a-b plane. These non-covalent interactions stabilized compound 7a in the crystalline state.

Kinetic UV-Vis Spectroscopic and DFT Mechanistic Study of the Redox Reaction of [OsVIIIO4(OH)n]n- (n = 1, 2) and Methanol in a Basic Aqueous Matrix.

This combined experimental and computational study builds on our previous studies to elucidate the reaction mechanism of methanol oxidation by OsVIII oxido/hydroxido species (in basic aqueous media) while accounting for the simultaneous formation of OsVII species via a comproportionation reaction between OsVIII and OsVI. UV-Vis spectroscopy kinetic analyses with either CH3OH or the deuterated analogue CD3OH as a reducing agent revealed that transfer of α-carbon-hydrogen of methanol is the partial rate-limiting step. The resulting relatively large KIE value of approximately 11.82 is a combination of primary and secondary isotope effects. The Eyring plots for the oxidation of these isotopologues of methanol under the same reaction conditions are parallel to each other and hence have the same activation enthalpy [Δ⧧H° = 14.4 ± 1.2 kcal mol-1 (CH3OH) and 14.5 ± 1.3 kcal mol-1 (CD3OH)] but lowered activation entropy (Δ⧧S°) from -12.5 ± 4.1 cal mol-1 K-1 (CH3OH) to -17.1 ± 4.4 cal mol-1 K-1 (CD3OH). DFT computational studies at the PBE-D3 level with QZ4P (Os) and pVQZ (O and H) basis sets provide clear evidence to support the data and interpretations derived from the experimental kinetic work. Comparative DFT mechanistic investigations in a simulated aqueous phase (COSMO) indicate that methanol and OsVIII first associate to form a noncovalent adduct bound together by intermolecular H-bonding interactions. This is followed by spin-forbidden α-carbon-hydrogen transfer (not O-H transfer) from methanol to OsVIII by means of HAT, which is found to be the partial rate-limiting step. Without the organic and inorganic fragments dissociating from each other during the entire stepwise redox reaction (in order to avoid formation of highly energetically unfavorable monomer species), the HAT step is followed by PT and then ET before the final product monomers formaldehyde and OsVI dissociate from each other. DFT-calculated Δ⧧H° is within 5 kcal mol-1 of the experimentally obtained value, while the DFT Δ⧧S° is three times larger than that found from the experiment.

Folding and duplex formation in mixed sequence recognition-encoded m-phenylene ethynylene polymers.

Oligomers equipped with complementary recognition units have the potential to encode and express chemical information in the same way as nucleic acids. The supramolecular assembly properties of m-phenylene ethynylene polymers equipped with H-bond donor (D = phenol) and H-bond acceptor (A = phosphine oxide) side chains have been investigated in chloroform solution. Polymerisation of a bifunctional monomer in the presence of a monofunctional chain stopper was used for the one pot synthesis of families of m-phenylene ethynylene polymers with sequences ADnA or DAnD (n = 1–5), which were separated by chromatography. All of the oligomers self-associate due to intermolecular H-bonding interactions, but intramolecular folding of the monomeric single strands can be studied in dilute solution. NMR and fluorescence spectroscopy show that the 3-mers ADA and DAD do not fold, but there are intramolecular H-bonding interactions for all of the longer sequences. Nevertheless, 1 : 1 mixtures of sequence complementary oligomers all form stable duplexes. Duplex stability was quantified using DMSO denaturation experiments, which show that the association constant for duplex formation increases by an order of magnitude for every base-pairing interaction added to the chain, from 103 M−1 for ADA·DAD to 105 M−1 for ADDDA·DAAAD. Intramolecular folding is the major pathway that competes with duplex formation between recognition-encoded oligomers and limits the fidelity of sequence-selective assembly. The experimental approach described here provides a practical strategy for rapid evaluation of suitability for the development of programmable synthetic polymers.

Design and Optimization of an Acyclic Amine Series of TRPV4 Antagonists by Electronic Modulation of Hydrogen Bond Interactions

Investigation of TRPV4 as a potential target for the treatment of pulmonary edema associated with heart failure generated a novel series of acyclic amine inhibitors displaying exceptional potency and PK properties. The series arose through a scaffold hopping approach, which relied on use of an internal H-bond to replace a saturated heterocyclic ring. Optimization of the lead through investigation of both aryl regions revealed approaches to increase potency through substituents believed to enhance separate intramolecular and intermolecular H-bond interactions. A proposed internal H-bond between the amine and neighboring benzenesulfonamide was stabilized by electronically modulating the benzenesulfonamide. In the aryl ether moiety, substituents para to the nitrile demonstrated an electronic effect on TRPV4 recognition. Finally, the acyclic amines inactivated CYP3A4 and this liability was addressed by modifications that sterically preclude formation of a putative metabolic intermediate complex to deliver advanced TRPV4 antagonists as leads for discovery of novel medicines.

Synthesis, Characterization of [Co(BDC)(Phen)H2O] and [Co(BDC)(DABCO)] MOFs, π..π Interactions, Hirshfeld Surface Analysis and Biological Activity

Mixed-ligand [Co(BDC)(Phen)(H2O)](1) and [Co(BDC)(DABCO)](2) MOFs were synthesized at 150 °C by solvothermal method. These MOFs analyzed by powder FT-IR, powder X-ray diffraction (PXRD), SEM and EDX and TGA-DTA analysis. The molecular structure confirmed by single-crystal XRD studies of 1 suggests a square planar structure with intermolecular π…π interaction between lateral 1,10-phenanthroline ring shows at a distance of 3.581 A and 3.560 A. Hirshfeld surfaces analysis of 1 mapped over dnorm displays extensive O–H/Co–O interactions and intermolecular H-bonding interactions. Antimicrobial activity of 1 is good comparatively with 2, attributed to the release of cation metal ions easily and more extended period. Antioxidant studies against DPPH scavenging ability are shown a maximum of 48.62% inhibition by 1. DNA cleavage activity of MOF 1 increases with the concentration increase.

Azobenzene Based Photo-responsive Mechanical Actuator Fabricated by Intermolecular H-bond Interaction

Photo-responsive mechanical actuator is a class of stimuli-responsive materials transferring light to mechanical energy through macroscopic transformation. To fabricate photo-responsive mechanical actuator, soft polymeric materials crosslinked with functional bridging structures are desired. Supramolecular interaction is a relatively common way to fabricate crosslinked materials due to its excellent self-assembly performance. And azobenzene and derivatives are ideal candidates of photo-responsive materials because of the unique photo-induced trans-cis isomerization. Here, a new kind of crosslinked materials based on supramolecular interaction between 4,4′-dihydroxyazobenzene and chitosan is reported. Under 355 nm irradiation, the macroscopic bending of polymeric materials occurs rapidly due to the photo-isomerization of 4,4′-dihydroxyazobenzene. Meanwhile, the photo-responsive mechanical actuator can also lift weight which is up to 200 times that of the actuator itself, and convert energy from light to mechanical work efficiently. This report suggests a new kind of photo-responsive actuator based on supramolecular interaction and may be helpful to contribute a theoretical basis to the design and synthesis of photo-responsive mechanical actuator suitable for large-scale manufacturing industrialization in future.

The Effect of HPMC and CNC on the Structure and Properties of Alginate Fibers

Bio-composite alginate fibers with binary and ternary blends were prepared by using cellulose nanocrystal (CNC) and hydroxypropyl methylcellulose (HPMC) as composite fillers through wet-spinning method. Structural, thermal, mechanical properties and surface morphology of fibers were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), Thermogravimetric Analysis (TGA), Mechanical strength testing, Scanning Electron Microscopy (SEM). The thermal stability and mechanical performance of SA/HPMC and SA/HPMC/CNC composite fibers improved as the increasing of crystallinity and intermolecular H-bonding interaction of the fibers. HPMC is helpful to improve the extensibility and stiffness of alginate fibers, and CNC can further enhance the stiffness of SA/HPMC composite fibers. The tensile strength, elongation at break, the initial modulus and work at break of SA/HPMC/CNC composite fibers were superior to those of alginate fibers. Roughness of surface and tensile section of SA/HPMC and SA/HPMC/CNC composite fibers got increased. Water absorbency and salt resistance were significantly improved.

Nucleobase-Tackified renewable plant oil-based supramolecular adhesives with robust properties both under ambient conditions and underwater

The development of sustainable functional materials derived from natural biomass is attracting tremendous attention from both academic and industrial fields in recent years. Besides renewability, sustainable polymeric materials are highly expected to outperform fossil fuel-derived analogues, showing the excellent application potentials. In this work, a renewable plant-oil based polymer was synthesized and its copolymers tackified by adenine/thymine-containing monomers could act as pressure sensitive adhesives (PSAs) with good performance attained. The PSAs containing adenine moieties had better adhesive properties compared with thymine-containing copolymers with the same molar ratio of comonomers, on account of its strong π-π stacking of purines. In addition, the supramolecular mixtures with complementary nucleobases could form intermolecular H-bonding interaction, having both enhanced peel and shear strengths over ones with individual nucleobases. The renewable plant oil-based PSAs showed outstanding reusability and robust adhesion to various substrates. More importantly, the long alkyl chains from the plant oil moieties also impart the adhesives with good hydrophobicity, which enables us to use the adhesives in the presence of water or even under water. This work highlights that the utilization of bio-inspired supramolecular interactions provides us with a straightforward and viable strategy for fabricating high performance biomass-based polymeric materials.

Intermolecular Hydrogen Bonding between Poly[(R)-3-hydroxybutyrate] (PHB) and Pseudoboehmite and Its Effect on Crystallization of PHB

In the present study, we focused on the intermolecular H-bonding interactions of poly[(R)-3-hydroxybutyrate (PHB) with an inorganic material, pseudoboehmite (PB), and its effect on PHB crystallizat...

Interpretation of hydrogen bonding formation through thermodynamic, spectroscopic and DFT studies between isoamyl alcohol and benzyl alcohol at T = (293.15 to 318.15) K

The density (ρ) and viscosity (η) data for the binary system of isoamyl alcohol (IAA) and benzyl alcohol (BA) were measured in the whole mole fraction at T = (293.15 to 318.15) K with the step of 5 K under atmospheric pressure. Excess molar volume (VmE), apparent molar volumes (Vm,∅, 1 and Vm,∅, 2), partial molar volumes (V¯m,1 and V¯m,2), excess partial molar volumes (V¯m,1E and V¯m,2E)and also viscosity deviation (∆η) were calculated by using the experimental values of density and viscosity of binary mixtures in the all above mentioned temperatures. The VmE and ∆η properties were fitted with the Redlich-Kister (R-K) equation. Excess molar volumes for the studied binary mixtures have a negative deviation from the ideal behavior over the entire mole fraction range. The effect of the temperature on the excess molar volumes and viscosity deviations are discussed and analyzed. Further, 1H NMR and FT-IR spectra and density functional theory (DFT) confirmed that there were intermolecular H-bonding interactions between IAA and BA in the binary mixture as (IAA)-O-H⋯⋯O-(BA) and (BA)-O-H⋯⋯O-(IAA).