Definition of the hydrogen bond (IUPAC Recommendations 2011)

Arunan, E.; Desiraju, Gautam R.; Klein, Roger A.; Sadlej, Joanna; Scheiner, Steve; Alkorta, Ibón; Clary, David C.; Crabtree, Robert H.; Dannenberg, J. J.; Hobza, Pavel; Kjaergaard, Henrik G.; Legon, A. C.; Mennucci, Benedetta; Nesbitt, David J.

doi:10.1351/pac-rec-10-01-02

Cited by 1,602 publications

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“…Hydrogen bonds (HBs) are by far the most frequently occurring and widely studied type of interaction [4,5]; other weak interactions that have traditionally received attention include π-π [6], cation-π [7], anion-π [8], and aurophilic [9] bonds. σ-Hole interactions [10][11][12] represent a relatively recent entry into the canon of weak bonds [13][14][15], but following the seminal papers of P. Politzer et al [16,17], these interactions rapidly became popular targets for studies in this field [15,[18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

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Modeling indicates the presence of a region of low electronic density (a Bσ-hole^) on group 14 elements, and this offers an explanation for the ability of these elements to act as electrophilic sites and to form attractive interactions with nucleophiles. While many papers have described theoretical investigations of interactions involving carbon and silicon, such investigations of the heavier group 14 elements are relatively scarce. The purpose of this review is to rectify, to some extent, the current lack of experimental data on interactions formed by germanium and tin with nucleophiles. A survey of crystal structures in the Cambridge Structural Database is reported. This survey reveals that close contacts between Ge or Sn and lone-pair-possessing atoms are quite common, they can be either intra-or intermolecular contacts, and they are usually oriented along the extension of the covalent bond formed by the tetrel with the most electron-withdrawing substituent. Several examples are discussed in which germanium and tin atoms bear four carbon residues or in which halogen, oxygen, sulfur, or nitrogen substituents replace one, two, or three of those carbon residues. These close contacts are assumed to be the result of attractive interactions between the involved atoms and afford experimental evidence of the ability of germanium and tin to act as electrophilic sites, namely tetrel bond (TB) donors. This ability can govern the conformations and the packing of organic derivatives in the solid state. TBs can therefore be considered a promising and robust tool for crystal engineering.

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Section: Introductionmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

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“…The Atoms in Molecules (AIM) analysis is important for the characterization of hydrogen bond as it was one of its criteria suggested by IUPAC [2]. AIM method [22] has became a practical tool for understanding the properties of hydrogen bonds in many cases.…”

Section: Aim Analysismentioning

confidence: 99%

“…The IUPAC recommends is using such name for the form of association X-HÁ Á ÁY between the electronegative atom Y and the hydrogen atom attached to the second atom X, and in which the electrostatic interactions play the key role [1]. Such definition does not cover all interactions in which the hydrogen atom is an essential element, but new, less restricted definition was published recently [2].…”

Section: Introductionmentioning

confidence: 99%

“…In general, conventional hydrogen-bond X-H moiety is define by X, which is more electronegative than H (i.e., O-H Á Á Á B, N-H Á Á Á B), while proton acceptor part B posses, for instant, electron pairs, as N, O, or F atoms. To study InHB nonconventional hydrogen bond we chose the molecule BeH 2 as an electron donor (with heavy electron-deficient atom), while LiH or LiF played a role of electron acceptor molecules [5]. The transfer of charge is thus in the same direction as the proton flow (i.e., from X-H to Y); therefore this interaction was called ''inverse,'' contrary to the conventional hydrogen bond (where transfer of charges is from the moiety Y to X-H moiety) [5,6].…”

Section: Introductionmentioning

confidence: 99%

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Inverse hydrogen bond: theoretical investigation on the nature of interaction and spectroscopic properties

Ilnicka

Sadlej

2012

Struct Chem

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A computational investigation was carried out to characterize the inverse (hydride) hydrogen bond in model complexes. Properties such as molecular structures and energetics have been studied by supermolecular MP2 approach. We focus on vibrational spectra, NMR shielding, and spin-spin coupling constants-signals that reflect the electronic structures of the compounds. The bonding in these complexes has been analyzed for a first time by SymmetryAdapted Perturbation Theory to provide the intricate insight into the nature of the interaction. The cyclic complexes, which have multiple interaction, are stable due to strong redistribution of electron density upon the complexation and differ from the linear ones by the induction energy as the most important term exceeding the electrostatic term. The linear complexes, which represent the inverse hydrogen bond, are characterized by much stronger induction than dispersion energy, contrary to the conventional hydrogen bonds, where these two terms happen to be of nearly equal magnitude. This result is the most noticeable difference between inverse and conventional hydrogen bonds.

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“…The main features are summed up below [9]: (1) forces that determine the formation of a hydrogen bond have an electrostatic origin, arise from charge transfer between the donor and acceptor, and involve the dispersion component;…”

Section: New Definition Of Hydrogen Bond: Progress and Unsolved Problemmentioning

confidence: 99%

Conjugation in hydrogen-bonded systems

Novakovskaya

2012

Struct Chem

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Analysis of the electron density distribution in clusters composed of hydrogen fluoride, water, and ammonia molecules, especially within the hydrogen-bond domains, reveals the existence of both σ-and π-binding between molecules. The σ-kind density distribution determines the mutual orientation of molecules. A π-system may be delocalized conjugated, which provides additional stabilization of molecular clusters. In those clusters where the sequence of hydrogen bonds is not planar, a peculiar kind of π-conjugation exists. HF − 2 and H 5 O + 2 ions are characterized by quasi-triple bonds between the electronegative atoms. The most long-lived species stabilized by delocalized π binding are rings and open or closed hoops composed of fused rings. It is conjugated π system that determines cooperativity phenomenon.

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Definition of the hydrogen bond (IUPAC Recommendations 2011)

Cited by 1,602 publications

References 1 publication

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Inverse hydrogen bond: theoretical investigation on the nature of interaction and spectroscopic properties

Conjugation in hydrogen-bonded systems

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