1,8-Chalcogen-bridged naphthalenes. Strong carbon bases in the gas phase

Sanz, Pablo; Yáñez, Manuel; Mó, Otília

doi:10.1039/b205601a

Cited by 33 publications

(23 citation statements)

References 41 publications

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“…[8] In addition, this element presents a variety of applications in alloys, such as tellurium-steel alloy, and in different electrical devices, such as IR detectors, [9] solar panel detectors and photovoltaic cells. [10] The numerous applications of the chalcogen atoms imposed a significant improvement in the study, both theoretical and experimental, of these atoms and their capacity to establish weak non-bonded interactions [11][12][13][14][15] within gas-phase molecules, [16] organic [17][18][19] and biological systems. [20] As a result of these investigations new compounds with novel bonding arrangements [21] have been discovered, presenting unprecedented structures.…”

Section: Introductionmentioning

confidence: 99%

Intermolecular Weak Interactions in HTeXH Dimers (X=O, S, Se, Te): Hydrogen Bonds, Chalcogen–Chalcogen Contacts and Chiral Discrimination

Sánchez‐Sanz¹,

Trujillo²,

Alkorta³

et al. 2012

ChemPhysChem

108

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A theoretical study of the HTeXH (X=O, S, Se and Te) monomers and homodimers was carried out by means of second-order Møller-Plesset perturbation theory (MP2) computational methods. In the case of monomers, the isomerization energy from HTeXH to H(2) Te=X and H(2) X=Te (X=O, S, Se, and Te) and the rotational transition-state barriers were obtained. Due to the chiral nature of these compounds, homo and heterochiral dimers were found. The electron density of the complexes was characterized with the atoms-in-molecules (AIM) methodology, finding a large variety of interactions. The charge transfer within the dimers was analyzed by means of natural bond orbitals (NBO). The density functional theory-symmetry adapted perturbation theory (DFT-SAPT) method was used to compute the components of the interaction energies. Hydrogen bonds and chalcogen-chalcogen interactions were characterized and their influence analyzed concerning the stability and chiral discrimination of the dimers.

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Section: Introductionmentioning

confidence: 99%

Intermolecular Weak Interactions in HTeXH Dimers (X=O, S, Se, Te): Hydrogen Bonds, Chalcogen–Chalcogen Contacts and Chiral Discrimination

Sánchez‐Sanz¹,

Trujillo²,

Alkorta³

et al. 2012

ChemPhysChem

108

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“…In particular, the field of compounds related to DMAN but with phosphorus instead of nitrogen atoms has been studied since their discovery in 1993 till today. Other weak interactions such as halogen bonds [35][36][37] and chalcogen bonds [38][39][40][41][42][43] can contribute to the stability of a given conformation. However, 1,8bisphosphor naphthalene derivatives and their protonated structures have been experimentally studied.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular pnicogen interactions in phosphorus and arsenic analogues of proton sponges

Sánchez‐Sanz

Trujillo

Alkorta

et al. 2014

Phys. Chem. Chem. Phys.

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A computational study of the intramolecular pnicogen bond in 1,8-bis-substituted naphthalene derivatives (ZXH and ZX2 with Z = P, As and X = H, F, Cl, and Br), structurally related to proton sponges, has been carried out. The aim of this paper is the study of their structural parameters, interaction energies and electronic properties such as electron density on the intramolecular interaction. The calculated geometrical parameters associated to the P···P interaction are in reasonably good agreement with the crystal structures found in a CSD search, in particular those of the halogen derivatives. Isodesmic reactions where the 1,8-bis-substituted derivatives are compared to monosubstituted derivatives have been calculated, indicating that the 1,8 derivatives are more stable than the monosubstituted ones for those cases with X-Z···Z-X and F-Z···Z-H alignments. Electron densities and Laplacians at the BCP on the pnicogen interactions suggest that they can be classified as pure closed shell interactions with a partial covalent character. Electron density shift maps are consistent with the results for intermolecular pnicogen interactions. Relationships between interatomic distance and electron density at the bond critical points and between interatomic distance and the orbital charge transfer stabilization energies have been found.

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“…Compound 86 a is predicted to be an oxygen base of similar basicity to proton sponges, whilst the remaining species are carbon bases, the para-atom with respect to the more electronegative peri-atom being the most basic site. [111] On a similar note, whilst 86 a is predicted to deprotonate at the para-C-H group, for all others the most favourable site for deprotonation is the ortho-C-H group. [112] The EÀE bond in C 3 E 2 ring of dithiole 82 a and diselenole 82 b can be reduced with NaBH 4 [113] or LiAlH 4 [113,114] with the formation of the respective dithiol 87 a or diselenol 87 b (Scheme 51).…”

Section: Synthesis and Reactivity Of Dichalcogenolesmentioning

confidence: 92%

“…[162] Computational studies on protonation and deprotonation of the oxochalcogenoles 86 a-d are mentioned above, [111,112] no other reports appeared in the literature on species of this type.…”

Section: Napso Systemsmentioning

confidence: 97%

Naphthalene and Related Systems peri‐Substituted by Group 15 and 16 Elements

Kilián

Knight

Woollins

2011

Chemistry A European J

118

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Synthetic and bonding aspects of heavier Group 15 (P, As, Sb, Bi) and 16 (S, Se, Te) peri-substituted naphthalenes, are discussed in this review. An important and unifying feature of the chemistry of these systems is the lively discussion about the nature of the interaction between peri-atoms. Are atoms bonded when they are closer than the sum of their van der Waals radii? Is there any (weak) bonding, or just a strained repulsive interaction? Positioning atoms of Group 15 and 16 at the naphthalene 1,8-positions provides leading systems with which to study these bonding issues.

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1,8-Chalcogen-bridged naphthalenes. Strong carbon bases in the gas phase

Cited by 33 publications

References 41 publications

Intermolecular Weak Interactions in HTeXH Dimers (X=O, S, Se, Te): Hydrogen Bonds, Chalcogen–Chalcogen Contacts and Chiral Discrimination

Intermolecular Weak Interactions in HTeXH Dimers (X=O, S, Se, Te): Hydrogen Bonds, Chalcogen–Chalcogen Contacts and Chiral Discrimination

Intramolecular pnicogen interactions in phosphorus and arsenic analogues of proton sponges

Naphthalene and Related Systems peri‐Substituted by Group 15 and 16 Elements

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