“…This red shift of transition displays existence of H- bonding between aromatic amines and anisole. Similar type of shifts was reported in the experimental study of same model complexes through ultrasonic application [9]. It was concluded from results that methylation of aniline and hydrogen bonding are responsible to shift π→π* transition towards higher wavelength.Fig.…”
Section: Resultssupporting
confidence: 84%
“…Therefore, total interaction energy of N-methylaniline complexes is higher than aniline complex is due to higher ionic character (electrostatic interaction) of N–H bond. But it was reported experimentally that aniline can form more stable complex than N-methylaniline with anisole [9]. This may be due to the ability of aniline to form 1:2 complex along with 1:1 complexes, which is more stable than 1:1 complexes of N-methylaniline.Fig.…”
Section: Resultsmentioning
confidence: 94%
“…Recently, we established the formation of hydrogen bonded complexes between anisole and aromatic amines through ultrasonic and UV spectral studies (experimental). We found from the thermodynamic data of these complexes that of the two complexes, aniline formed more stable complex with anisole than N-methylaniline [9].…”
Theoretical investigations have been performed on hydrogen (H-) bonded complexes of two aromatic amines with anisole to investigate the effect of the methyl substituent on N – H⋯O and N – –H⋯π interactions. Natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) analyses were done to elucidate the nature of H- bonding. In 1:1 complexes, the total interaction energy of N-methylaniline complex is higher than that of aniline complex. The existence of bond critical point between N–H of amine and oxygen of anisole confirms weak hydrogen bonding. The energy decomposition analysis showed the role of CT in stabilizing complexes.
“…This red shift of transition displays existence of H- bonding between aromatic amines and anisole. Similar type of shifts was reported in the experimental study of same model complexes through ultrasonic application [9]. It was concluded from results that methylation of aniline and hydrogen bonding are responsible to shift π→π* transition towards higher wavelength.Fig.…”
Section: Resultssupporting
confidence: 84%
“…Therefore, total interaction energy of N-methylaniline complexes is higher than aniline complex is due to higher ionic character (electrostatic interaction) of N–H bond. But it was reported experimentally that aniline can form more stable complex than N-methylaniline with anisole [9]. This may be due to the ability of aniline to form 1:2 complex along with 1:1 complexes, which is more stable than 1:1 complexes of N-methylaniline.Fig.…”
Section: Resultsmentioning
confidence: 94%
“…Recently, we established the formation of hydrogen bonded complexes between anisole and aromatic amines through ultrasonic and UV spectral studies (experimental). We found from the thermodynamic data of these complexes that of the two complexes, aniline formed more stable complex with anisole than N-methylaniline [9].…”
Theoretical investigations have been performed on hydrogen (H-) bonded complexes of two aromatic amines with anisole to investigate the effect of the methyl substituent on N – H⋯O and N – –H⋯π interactions. Natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) analyses were done to elucidate the nature of H- bonding. In 1:1 complexes, the total interaction energy of N-methylaniline complex is higher than that of aniline complex. The existence of bond critical point between N–H of amine and oxygen of anisole confirms weak hydrogen bonding. The energy decomposition analysis showed the role of CT in stabilizing complexes.
“…24,26,27 Extensive investigations have been carried out on the interactions of structurally different amines with aliphatic, aromatic, and alicyclic ethers. [21][22][23]28,29 This work is the extension of our earlier report on npropylamine (NPA)−ether interactions, 30 and now it is aimed at correlating the strength of interactions in two ternary liquid systems containing different equimolal concentrations of isopropylamine (IPA) with two aryl ethers, anisole (ANI) and diphenylether (DPE), in n-hexane (n-Hex) solvent. Isopropylamine is a structural isomer of NPA, and it has several industrial applications.…”
Section: Introductionmentioning
confidence: 96%
“…Recently, we have reported a series of investigations on the intermolecular hydrogen-bonded complexes between certain amines with different ethers, ketones, and aldehydes in a nonpolar solvent medium. − Primary and secondary amines form hydrogen-bonded complexes with organic compounds containing hydrogen acceptors. ,, Extensive investigations have been carried out on the interactions of structurally different amines with aliphatic, aromatic, and alicyclic ethers. − ,, …”
Hydrogen bonded complexes of isopropylamine (IPA) with two aromatic ethers, namely, anisole (ANI) and diphenyl ether (DPE), are analyzed from the results obtained from acoustical parameters and density functional theory (DFT) computations. This type of investigation envisages the presence of various interactions existing in these complexes. The measurements of speed of sound (u), density (ρ), and dynamic viscosity (η) were made accurately for two ternary liquid systems containing equal molality of isopropylamine (IPA) and two structurally different ethers in n-hexane solvent at 303.15 K and 101 kPa pressure. Acoustical and excess parameters were calculated from the measured data. The extent of complex formation increases with concentration and is found to be more in the IPA−ANI system than in the IPA−DPE system. The two aromatic ethers favor the complex formation, though they are found to be relatively less stable than the complexes of these ethers with n-propylamine, which may be due to steric hindrance in IPA and weakening of the complex formation. The association of solute components in the two systems through noncovalent interactions is analyzed comprehensively in this paper at molecular-level insights through DFT parameters. The stable and lowest-energy structures of complexes in n-hexane medium were obtained through DFT. Bond parameters and the energy of complexation were analyzed. The data obtained from both the ultrasonic study and DFT method are comparable and showed structural dependence on molecular association in the two systems. This study also confirms the dominance of the steric effect over the inductive effect in the IPA−DPE system compared to that in the IPA−ANI system.
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