Conformational stability, molecular structure, intramolecular hydrogen bonding, and vibrational spectra of 5,5-dimethylhexane-2,4-dione

Vakili, Mohamad; Tayyari, Sayyed Faramarz; Kanaani, Ayoub; Nekoei, Abdo-Reza; Salemi, Sirous; Miremad, H.; Berenji, Ali Reza; Sammelson, Robert Erik

doi:10.1016/j.molstruc.2011.04.045

Cited by 18 publications

(4 citation statements)

References 45 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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“…After that, many theoretical and experimental works have been done to study the properties of intramolecular and intermolecular hydrogen bond [2][3][4][5][6] . In an intramolecular hydrogen bond (IHB) system, both proton donor and proton acceptor groups are located in the same molecule.…”

Section: Introductionmentioning

confidence: 99%

Correlation Between Parameters Related to Intramolecular Hydrogen Bond Strength and Hammett Constant in Para Substituted Benzoylacetone (A Theoretical and Experimental Study)

Darugar¹,

Vakili²,

Tayyari³

et al. 2017

Orient. J. Chem

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Conformational stability, equilibrium constant between two stable cis-enol forms, and intramolecular hydrogen bonding (IHB) of benzoylacetone (BA) and p-substituted benzoylacetone (X-BA), where X=NO 2 , OCH 3 , CH 3 , OH, CF 3 , Cl, F, and NH 2 , have been investigated by means of density functional theory (DFT) calculations and compared with the reported experimental results. According to our calculations, the energy difference between the two stable chelated enol forms is negligible, about 0.35-1.1 kcal/mol ranges in the gas phase and different solvents. The electronic effects of p-substituted benzoylacetone on IHB strength were determined and established by NMR, IR spectra, geometry, and topological parameters with Hammett linear free energy relationships. Also, the linear correlation coefficients between σ p and selected parameters related to IHB strength, such as geometrical, topological parameters, IR and NMR spectroscopic data, and NBO results related to IHBs were considered. Good linear correlations between σ p and the mentioned parameters were obtained

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Conformational stability, molecular structure, intramolecular hydrogen bonding, and vibrational spectra of 5,5-dimethylhexane-2,4-dione

Cited by 18 publications

References 45 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

Correlation Between Parameters Related to Intramolecular Hydrogen Bond Strength and Hammett Constant in Para Substituted Benzoylacetone (A Theoretical and Experimental Study)

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