Nature of the E⋯E′ interactions (E, E′ = O, S, Se, and Te) at naphthalene 1,8-positions with fine details of the structures: experimental and theoretical investigations

Abstract

The nature of E⋯E′ in 1-RE–8-R′E′C10H6 (E/E′ = O, S, Se and Te) is clarified with the QTAIM approach and NBO analysis, after structural determinations.

Quantum chemical analysis of noncovalent bonds within crystals. Concepts and concerns

“…Some NBO quantities, particularly the secondorder perturbation energy associated with the transfer in question, have found widespread application in estimating bond energies in HBs [59][60][61] and other noncovalent bonds. [62][63][64] Despite its usefulness, it is problematic to equate this NBO measure of charge transfer with the actual bond energy. In the first place, NBO concerns itself only with one element of the full interaction, viz.…”

“…Some NBO quantities, particularly the second-order perturbation energy associated with the transfer in question, have found widespread application in estimating bond energies in HBs 59–61 and other noncovalent bonds. 62–64…”

Chalcogen controlled redox behaviour in peri-substituted S, Se and Te naphthalene derivatives

“…A wide range of possible conformations have been encountered, or considered computationally, amongst the different peri-substituted phenylchalcogenides A1-N12 over the three charge states, 36 species in all. The definitions and labels employed for these conformations, using a widely adopted approach, are depicted in Scheme 1; 2,7,59,62,63 this scheme can also be used for N13-N16, the halo-derivatives, by replacement of one PhE group by X = Br or I, thereby reducing the number of possible conformers. 62 Geometries were defined as follows; each of the phenyl rings could be (independently) located perpendicular to the plane of the aromatic structure (A), parallel to the plane (B) or between these two extremes (C).…”

“…There is ongoing interest in the structural, bonding and reactivity implications of main group elements placed into the peri-positions of polycyclic aromatic scaffolds, of which naphthalene-1,8-diyl and acenaphthene-5,6-diyl derivatives (see Chart 1) are the most common. [1][2][3][4][5][6][7][8][9] Pioneering work, including electrochemistry, on the naphthalene series was undertaken by Fujihara and Furukawa in the 1990's, 10,11 following on earlier work from the same group and from Glass on redox chemistry of chalcogens incorporated into aliphatic heterocycles. 12 Applications include catalysis at cationic tellurium 13 and ditellurium 14 compounds and the unique coordination environment afforded by a phosphorus bridged dinaphthalene ligand with an envelope conformation.…”

The nature of G⋯E–Y σ(3c–4e) in o-MenGCH2C6H4EY (MenG = Me2N and MeE; E = O, S, Se and Te; Y = F, Cl, Br, EMe and Me) with contributions from CT and compliance constants in noncovalent G⋯E interactions

“…The chemistry originating from GEY σ(3c–4e) in the naphthalene 1,8-positions of 8-G–C 10 H 6 –EY-1 (I) has been studied thoroughly by Wakayama group. 11 The linear alignment of the three GEY atoms was called “G-dependence”, especially for Y = C, and the donor ability for G = F is demonstrated. The nature of G⋯E–Y in I is clarified, which is discussed elsewhere.…”