Angular dependence of hydrogen bond energy in neutral and charged systems containing CH and NH proton donors

Nepal, Binod; Scheiner, Steve

doi:10.1016/j.cplett.2015.04.041

Cited by 7 publications

(8 citation statements)

References 42 publications

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“…They were computed to be´4.74 kcal/mol for NH¨¨¨O and´2.06 kcal/mol for CH¨¨¨O, a little less than half the NH¨¨¨O value. These values correspond nicely with other calculations designed to compute these HB energies in other systems [60,68,81,[94][95][96]. The substantial interaction energy for NH···O comes even at the expense of a H-bond that suffers certain distortions from the intermolecular orientation it would adopt in the absence of intramolecular constraints associated with the full molecule I.…”

Section: Direct Evaluation Of H-bond Energiessupporting

confidence: 67%

Analysis of Hydrogen Bonds in Crystals

2016

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Section: Direct Evaluation Of H-bond Energiessupporting

confidence: 67%

Analysis of Hydrogen Bonds in Crystals

2016

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“…They were computed to be −4.74 kcal/mol for NH···O and −2.06 kcal/mol for CH···O, a little less than half the NH···O value. These values correspond nicely with other calculations designed to compute these HB energies in other systems [60,68,81,[94][95][96]. The substantial interaction energy for NH···O comes even at the expense of a H-bond that suffers certain distortions from the intermolecular orientation it would adopt in the absence of intramolecular constraints associated with the full molecule I.…”

Section: Direct Evaluation Of H-bond Energiessupporting

confidence: 64%

Dissection of the Factors Affecting Formation of a CH∙∙∙O H-Bond. A Case Study

Scheiner

2015

Crystals

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Quantum calculations are used to examine how various constituent components of a large molecule contribute to the formation of an internal CH···O H-bond. Such a bond is present in the interaction between two amide units, connected together by a series of functional groups. Each group is removed one at a time, so as to monitor the effect of each upon the H-bond, and thereby learn the bare essentials that are necessary for its formation, as well as how its presence affects the overall molecular structure. Also studied is the perturbation caused by change in the length of the aliphatic chain connecting the two amide groups. The energy of the CH···O H-bond is calculated directly, as is the rigidity of the entire molecular framework.

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“…Notably, further much smaller, attractive components, such as the London dispersion, are not included in this estimate; thus, for very weak hydrogen‐bonding contacts, repulsive estimates are expected. This is mostly the case if the corresponding N1⋅⋅⋅H−X angle deviates strongly from the optimum 180° region, [70] which is the case for most of the presented model systems (cf. Figures 8 and 9 a, ϕ (N1⋅⋅⋅H‐X) mean =136°, Table 1).…”

Section: Resultsmentioning

confidence: 81%

Quantification of Noncovalent Interactions in Azide–Pnictogen, –Chalcogen, and –Halogen Contacts

Bursch

Kunze

Vibhute

et al. 2021

Chemistry A European J

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The noncovalent interactions between azides and oxygen‐containing moieties are investigated through a computational study based on experimental findings. The targeted synthesis of organic compounds with close intramolecular azide–oxygen contacts yielded six new representatives, for which X‐ray structures were determined. Two of those compounds were investigated with respect to their potential conformations in the gas phase and a possible significantly shorter azide–oxygen contact. Furthermore, a set of 44 high‐quality, gas‐phase computational model systems with intermolecular azide–pnictogen (N, P, As, Sb), –chalcogen (O, S, Se, Te), and –halogen (F, Cl, Br, I) contacts are compiled and investigated through semiempirical quantum mechanical methods, density functional approximations, and wave function theory. A local energy decomposition (LED) analysis is applied to study the nature of the noncovalent interaction. The special role of electrostatic and London dispersion interactions is discussed in detail. London dispersion is identified as a dominant factor of the azide–donor interaction with mean London dispersion energy‐interaction energy ratios of 1.3. Electrostatic contributions enhance the azide–donor coordination motif. The association energies range from −1.00 to −5.5 kcal mol−1.

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Angular dependence of hydrogen bond energy in neutral and charged systems containing CH and NH proton donors

Cited by 7 publications

References 42 publications

Analysis of Hydrogen Bonds in Crystals

Analysis of Hydrogen Bonds in Crystals

Dissection of the Factors Affecting Formation of a CH∙∙∙O H-Bond. A Case Study

Quantification of Noncovalent Interactions in Azide–Pnictogen, –Chalcogen, and –Halogen Contacts

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