Reinvestigation of intramolecular hydrogen bond in malonaldehyde derivatives: An ab initio, AIM and NBO study

Nowroozi, Alireza; Raissi, Heidar; Hajiabadi, H.; Jahani, Peyman Mohammadzadeh

doi:10.1002/qua.22635

Cited by 43 publications

(33 citation statements)

References 30 publications

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“…It is noteworthy that the estimation of the О─Н⋯О═С IMHB energy in the malonaldehyde 1b by the MTA method matches quantitatively with the energy difference between its open and closed rotamers (see Scheme ) . The reason for this coincidence is that both the σ‐ and π‐components of the RAHB interaction appear only in the closed form of malonaldehyde 1b .…”

Section: Resultssupporting

confidence: 54%

Quantitative decomposition of resonance‐assisted hydrogen bond energy in β‐diketones into resonance and hydrogen bonding (π‐ and σ‐) components using molecular tailoring and function‐based approaches

Afonin

Vashchenko

2020

J Comput Chem

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Using the molecular tailoring and function‐based approaches allows one to divide the energy of the O─H⋯O═C resonance‐assisted hydrogen bond in a series of the β‐diketones into resonance and hydrogen bonding components. The magnitude of the resonance component is assessed as about 6 kcal mol−1. This value increases by ca. 1 kcal mol−1 on going from the weak to strong resonance‐assisted hydrogen bonding. The magnitude of the hydrogen bonding component varies in the wide range from 2 to 20 kcal mol−1 depending on the structure of the β‐diketone in question.

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Section: Resultssupporting

confidence: 54%

Quantitative decomposition of resonance‐assisted hydrogen bond energy in β‐diketones into resonance and hydrogen bonding (π‐ and σ‐) components using molecular tailoring and function‐based approaches

Afonin

Vashchenko

2020

J Comput Chem

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“…This means that the conformer change should not lead to significant changes in the values of geometric parameters. In order to overcome any inaccuracies, another approach is to use more than just two conformers of a given molecule [ 47 , 60 , 61 , 62 , 63 ]. This idea will be shown on the example of 3-aminopropenal (3-aminoacrolein), which has four conformers.…”

Section: Theoretical Methods Of Estimating the Energy Of Intramolementioning

confidence: 99%

A Critical Overview of Current Theoretical Methods of Estimating the Energy of Intramolecular Interactions

Jabłoński

2020

Molecules

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This article is probably the first such comprehensive review of theoretical methods for estimating the energy of intramolecular hydrogen bonds or other interactions that are frequently the subject of scientific research. Rather than on a plethora of numerical data, the main focus is on discussing the theoretical rationale of each method. Additionally, attention is paid to the fact that it is very often possible to use several variants of a particular method. Both of the methods themselves and their variants often give wide ranges of the obtained estimates. Attention is drawn to the fact that the applicability of a particular method may be significantly limited by various factors that disturb the reliability of the estimation, such as considerable structural changes or new important interactions in the reference system.

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“…Such situations include, for example, intramolecular hydrogen bonds (or other noncovalent interactions) and systems of two molecules which are bonded by two or more intermolecular noncovalent interactions (for instance, Watson‐Crick base pairs). There are several procedures which allow the bond energy estimates in these special cases, among them the group of methods based on the comparison of energies of rotamers with and without the hydrogen bond (“closed” and “open” rotamers, respectively) including the related rotamers method, the isodesmic reactions method, and the molecular tailoring approach . However, all these methods are not universal, and their application strongly depends on the type of the structure under investigation.…”

Section: Introductionmentioning

confidence: 99%

Can halogen bond energy be reliably estimated from electron density properties at bond critical point? The case of the (A)_nZ—Y•••X⁻(X, Y = F, Cl, Br) interactions

Kuznetsov

2018

Int J of Quantum Chemistry

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Relationships between the Y•••X bond critical point (BCP) properties or the Y•••X distance and the halogen bond interaction energy were analyzed in detail by theoretical methods for the series of structures [(A)nZ—Y•••X]− (X,Y = F, Cl, Br; totally 441 structures). No relationship was found for the whole set of structures or for the series [(A)nZ—F•••X]−, [(A)nZ—Cl•••X]−, and [(A)nZ—Br•••X]−. The interaction energies may be roughly estimated from the BCP properties for the series [(A)nZ—Y•••F]−, [(A)nZ—Y•••Cl]−, and [(A)nZ—Y•••Br]− as well as for [(A)nZ—Y•••X]− (when (A)nZ is variable, X and Y are constant) with the mean absolute deviation values 2.04‐4.38 kcal/mol. The corresponding recommended relationships are provided and they are significantly different from the popular dependencies deduced previously for other types of noncovalent interactions. Tremendous effect of the computational method and basis set on the relationships under analysis was discovered. Computational results clearly indicate that, for practical purposes, the Eint(BCP property) dependencies should be established not simply for each global type of interactions (hydrogen bond, halogen bond, chalcogen bond, etc.) but for each combination of the first and second order atoms taking into account also the computational method and basis set.

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Reinvestigation of intramolecular hydrogen bond in malonaldehyde derivatives: An ab initio, AIM and NBO study

Cited by 43 publications

References 30 publications

Quantitative decomposition of resonance‐assisted hydrogen bond energy in β‐diketones into resonance and hydrogen bonding (π‐ and σ‐) components using molecular tailoring and function‐based approaches

Quantitative decomposition of resonance‐assisted hydrogen bond energy in β‐diketones into resonance and hydrogen bonding (π‐ and σ‐) components using molecular tailoring and function‐based approaches

A Critical Overview of Current Theoretical Methods of Estimating the Energy of Intramolecular Interactions

Can halogen bond energy be reliably estimated from electron density properties at bond critical point? The case of the (A)_nZ—Y•••X⁻(X, Y = F, Cl, Br) interactions

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Reinvestigation of intramolecular hydrogen bond in malonaldehyde derivatives: An ab initio, AIM and NBO study

Cited by 43 publications

References 30 publications

Quantitative decomposition of resonance‐assisted hydrogen bond energy in β‐diketones into resonance and hydrogen bonding (π‐ and σ‐) components using molecular tailoring and function‐based approaches

Quantitative decomposition of resonance‐assisted hydrogen bond energy in β‐diketones into resonance and hydrogen bonding (π‐ and σ‐) components using molecular tailoring and function‐based approaches

A Critical Overview of Current Theoretical Methods of Estimating the Energy of Intramolecular Interactions

Can halogen bond energy be reliably estimated from electron density properties at bond critical point? The case of the (A)nZ—Y•••X−(X, Y = F, Cl, Br) interactions

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Can halogen bond energy be reliably estimated from electron density properties at bond critical point? The case of the (A)_nZ—Y•••X⁻(X, Y = F, Cl, Br) interactions