Calculation of intramolecular hydrogen bonding strength and natural bond orbital (NBO) analysis of naphthazarin with chlorine substitution

Zahedi-Tabrizi, Mansoureh; Farahati, Razieh

doi:10.1016/j.comptc.2011.09.034

Cited by 12 publications

(11 citation statements)

References 49 publications

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“…1 After this, large number of theoretical and experimental studies have been conducted to investigate the properties of intramolecular and intermolecular hydrogen bonding. [2][3][4][5][6] This type of bond occurs in both inorganic molecules such as water and organic molecules such as DNA; and plays important roles in biological systems, biochemical reactions, transformation of genetic information, etc. 7 In an intramolecular hydrogen bond (IHB) system, both proton donor and proton acceptor groups, which may be of various kinds of functional groups, are located in the same molecule.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of intramolecular hydrogen bonding in the halo derivatives of 1-amino-3-imino-prop-1-ene

Emamian

Tayyari

2013

J Chem Sci

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Intramolecular hydrogen bonding (IHB) of 1-amino-3-imino-prop-1-ene (AIP), as the simplest resonance-assisted hydrogen bond system in symmetric N-H• • •N class, and its halo derivatives (F, Cl, and Br) have been studied at the DFT-B3LYP/6-311++G * * level of theory. For better understanding of the nature of substituent effects, nitro and methoxy derivatives of AIP were also added to our consideration. Good linear correlations between IHB energies based on Espinosa's equation and −G(r)/V (r) values, total electronic density, Laplacian of total electronic density in critical points, π-electron delocalization parameter (Q), hyper conjugative interaction energy of lp(N) → σ * (N-H), (F i, j /S i, j) 2 parameter, natural charges of bridged hydrogen, frequency shift of the N-H stretching vibration, and chemical shift of bridged hydrogen were obtained. Keywords. Intramolecular hydrogen bond; 1-amino-3-imino-prop-1-ene (AIM); density functional theory (DFT); natural bond orbital analysis (NBO).

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Section: Introductionmentioning

confidence: 99%

Theoretical study of intramolecular hydrogen bonding in the halo derivatives of 1-amino-3-imino-prop-1-ene

Emamian

Tayyari

2013

J Chem Sci

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“…In 1919, the concept of hydrogen bond had been proposed by Huggins [1]. After that, the properties of intramolecular and intermolecular hydrogen bonded systems have been studied theoretically and experimentally by several workers [2][3][4][5][6]. The cis-enol forms of β-diketones are engaged in an intramolecular hydrogen bond, IHB, system [7,8], which, as resulted by Gilli et al [9][10][11][12], the π-electron delocalization between the donor and acceptor atoms is responsible to increase the intramolecular HB strength in malonaldehyde, βdiketones and derivatives.…”

Section: Introductionmentioning

confidence: 99%

Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates

et al. 2018

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The stability of two stable cis-enol forms in two categories of β-diketones, including para-substituted of trifluorobenzoylacetone (X-TFBA) and 1-aryl-1,3-diketone malonates (X-ADM, X: H, NO2, OCH3, CH3, OH, CF3, F, Cl, and NH2) has been obtained by different theoretical methods. According to our results, the energy difference between the mentioned stable chelated enol forms for the titled compounds is negligible. The theoretical equilibrium constants between the two stable cis-enol of the mentioned molecules are in excellent agreement with the reported experimental equilibrium constant. In addition, the effect of different substitutions on the intramolecular hydrogen bond strength has been evaluated. The correlation between Hammett para-substituent constants, σp. with the theoretical and experimental parameters related to the strength of hydrogen bond in p-X-TFBA and p-X-ADM molecules also investigated by means of density functional theory calculations. The electronic effects of para-substitutions on the intramolecular hydrogen bond strength were determined by NMR and IR data related to intramolecular hydrogen bond strength, geometry, natural bond orbital results, and topological parameters. These parameters were correlated with the Hammett para-substituent constants, σp. Good linear correlations between σp and the several parameters related to the hydrogen bond strength, in this study were obtained.

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“…A computational study by Zahedi-Tabrizi and Farahati (2011) reported an increase in the strength of intermolecular hydrogen bonding with increase in the number of chlorine atoms in a compound. 21 Biodegradation of poly-chlorinated compounds is difficult because of their stability and toxic nature. 22,23 Furukawa et al related the degree of chlorination in 31 isomers of poly-chlorinated biphenyl (PCBs) to their biodegradation potential and found an inverse relation between biodegradation potential and the number of chlorine atoms in the molecule.…”

Section: Introductionmentioning

confidence: 99%

Reductive dechlorination of endosulfan isomers and its metabolites by zero-valent metals: reaction mechanism and degradation products

Singh

Bose

2017

RSC Adv.

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Calculation of intramolecular hydrogen bonding strength and natural bond orbital (NBO) analysis of naphthazarin with chlorine substitution

Cited by 12 publications

References 49 publications

Theoretical study of intramolecular hydrogen bonding in the halo derivatives of 1-amino-3-imino-prop-1-ene

Theoretical study of intramolecular hydrogen bonding in the halo derivatives of 1-amino-3-imino-prop-1-ene

Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates

Reductive dechlorination of endosulfan isomers and its metabolites by zero-valent metals: reaction mechanism and degradation products

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