1111098-36-2Relevant academic research and scientific papers
Synthetic and structural studies of 1, 8-chalcogen naphthalene derivatives
Knight, Fergus R.,Fuller, Amy L.,Buehl, Michael,Slawin, Alexandra M. Z.,Woollins, J. Derek
supporting information; experimental part, p. 7503 - 7516 (2010/08/20)
Four novel 1,8-disubstituted naphthalene derivatives 4-7 that contain chalcogen atoms occupying the peri positions have been prepared and fully characterised by using X-ray crystallography, multinuclear NMR spectroscopy, IR spectroscopy and MS. Molecular distortion due to noncovalent substituent interactions was studied as a function of the bulk of the interacting chalcogen atoms and the size and nature of the alkyl group attached to them. X-ray data for 4-7 was compared to the series of known 1, 8-bis(phenylchalcogeno) naphthalenes 1-3, which were themselves prepared from novel synthetic routes. A general increase in the E-E' distance was ob-served for molecules containing bulkier atoms at the peri positions. The decreased S...S distance from phenyl-1 and ethyl-4 analogues is ascribed to a weaker chalcogen lone pair-lone pair repulsion acting in the ethyl analogue due to the presence of two equatorial S(naphthyl) ring conformations. Two novel pen-substituted naphthalene sulfoxides of 1, Nap(O=SPh)(SPh) 8 and Nap(O=SPh)2 9, which contain different valence states of sulfur, were pre-pared and fully characterised by using X-ray crystallography and multinuclear NMR spectroscopy, IR spectroscopy and MS. Molecular structures were analysed by using naphthalene ring torsions, peri-atom displacement, splay angle magnitude, S...S interactions, aromatic ring orientations and quasi-linear O=S...S arrangements. The axial S(naphthyl) rings in 8 and 9 are unfavourable for S-S contacts due to stronger chalcogen lone pair-lone pair repulsion. Although quasi-linear O=S...S alignments suggest attractive interaction is conceivable, analysis of the B3LYP wavefunctions affords no evidence for direct bonding interactions between the S atoms.
How does non-covalent Se...Se=O interaction stabilize selenoxides at naphthalene 1,8-positions: Structural and theoretical investigations
Hayashi, Satoko,Nakanishi, Waro,Furuta, Atsushi,Drabowicz, Jozef,Sasamori, Takahiro,Tokitoh, Norihiro
experimental part, p. 196 - 206 (2009/03/12)
Bis-selenides (LL), such as 8-[MeSe(X)]-1-[MeSe(Z)]C10H 6 (1 (LL)), 8-[EtSe(X)]-1-[EtSe(Z)]C10H6 (2 (LL)), 8-[p-YC6H4Se(X)]-1-[MeSe(Z)]C10H 6 (3 (LL)) and 8-[p-YC
Noncovalent Z...Z (Z = O, S, Se, and Te) interactions: How do they operate to control fine structures of 1,8-dichalcogene-substituted naphthalenes?
Hayashi, Satoko,Nakanishi, Waro
experimental part, p. 1605 - 1615 (2009/05/06)
Homonuelear Z...Z (Z = O, S, Se, and Te) interactions are investigated employing naphthalene 1,8-positions in l,8-(MeZ)2C 10H6 (la-ld: Z = O (a), S (b), Se (c), and Te (d)), l-MeZ-8-PhZe10H6 (2a-2c). and l,8-(PhZ)2C 10H6 (3a-3d). Three types of structures are detected for la-3d: BB for la, CC for lb, lc, 2c, and 3d, and AB for 2a, 2b, and 3a-3c, in our definition, by X-ray crystallographic analysis, although some have already been reported. Quantum chemical calculations are performed on la-1d and 3c, together with model c, Me(H)Se...Se(H)Me, to elucidate how the fine structures are controlled by the interactions. AB are stabilized by the n p(Z)... σ*(Z-C) 3c-4e interactions for Z = S, Se, and Te. While CC are substantially stabilized by the n(Z) ...σ*(Z-C) interactions, they are well summarized as the disappearance of the nodal plane in π* (Z...z.). Factors to control the fine structures are clarified and visualized using the HOMO or HOMO-1 of model c. The energy profile of model c helps us to imagine the whole picture of the noncovalent Se...Se interactions.
