2017
DOI: 10.3390/molecules22010083
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Spectroscopic, DFT, and XRD Studies of Hydrogen Bonds in N-Unsubstituted 2-Aminobenzamides

Abstract: The structures of the mono- and the dihalogenated N-unsubstituted 2-aminobenzamides were characterized by means of the spectroscopic (1H-NMR, UV-Vis, FT-IR, and FT-Raman) and X-ray crystallographic techniques complemented with a density functional theory (DFT) method. The hindered rotation of the C(O)–NH2 single bond resulted in non-equivalence of the amide protons and therefore two distinct resonances of different chemical shift values in the 1H-NMR spectra of these compounds were observed. 2-Amino-5-bromoben… Show more

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Cited by 11 publications
(7 citation statements)
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“…The strong charge transfer interaction through the π-conjugated system led to substantial ground state donor-acceptor mixing and the appearance of a charge transfer band in the electron absorption spectrum. A partial double bond character for the C-N bond of primary amides is always invoked to account for the hindered rotation [24], and is therefore the cause of the nonequivalence of the resonances for the amide hydrogen atoms observed in their 1 H-NMR spectra [13,15]. Although the resonance interaction model provides a convenient explanation for the stabilization of the amino-carbonyl moiety, the changes in electron population and structure on rotation were previously found not to be in accord with an electron donation from the amino group to the carbonyl oxygen of formamide [26].…”
Section: Optimized Structures Of 2a 2b and 2c From Dft Analysesmentioning
confidence: 99%
“…The strong charge transfer interaction through the π-conjugated system led to substantial ground state donor-acceptor mixing and the appearance of a charge transfer band in the electron absorption spectrum. A partial double bond character for the C-N bond of primary amides is always invoked to account for the hindered rotation [24], and is therefore the cause of the nonequivalence of the resonances for the amide hydrogen atoms observed in their 1 H-NMR spectra [13,15]. Although the resonance interaction model provides a convenient explanation for the stabilization of the amino-carbonyl moiety, the changes in electron population and structure on rotation were previously found not to be in accord with an electron donation from the amino group to the carbonyl oxygen of formamide [26].…”
Section: Optimized Structures Of 2a 2b and 2c From Dft Analysesmentioning
confidence: 99%
“…The equilibrium geometries of the reactants, intermediates, transition states, and products were optimized by employing B3LYP/6-31G(d,p). DFT is a computational method that derives the properties of a system based on the electron density of the system [31,32]. The B3LYP functional with a 6-31G(d,p) basis set has been proven to be an appropriate choice for modeling organic species [31,33].…”
Section: Methodsmentioning
confidence: 99%
“…Palm kernel shell and coconut kernel shell powder is introduced into the polymer matrix according to the suggested ratio in Table 1. The experimental conditions as listed in Table 1 were selected based on the optimum conditions from previous researchers [7][8][9]. The solutions were then poured into a mold and dried at 40 o C for 1 days before being demoulded.…”
Section: Preparation Of Pva/pks/cks Epncs Using Solution Casting Methodsmentioning
confidence: 99%