peri-Interactions in Naphthalenes, 11 . A New Approach to the Investigation of Dative peri Bonding/A New Approach to the Investigation of Dative peri Bonding

Abstract

The failure of the sum of van der Waals radii axiom to provide information about donor-acceptor interactions in 8-dimethylamino-naphth-1-yl phosphines and their derivatives called for alternative methods. The coupling constants J(C,H) of the Me2N groups proved useful and indicate that in these compounds, N→P interactions are negligible.

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

“…Anisochronicity of the NMe 2 methyl groups in 1 H NMR was explained by hindered rotation, since peri-naphthalenes lacking the possibility of an intersubstituent dative bond showed the same non-equivalence. Other arguments, such as high-field shift of the phosphorus NMR signal on intramolecular DAN coordination (or its absence) were questioned by Schiemenz; additional support for non-existence of the dative bond was found in analysing the J(CH) coupling constants of NMe 2 groups [64] or the study of NMR properties of protonated DAN-phosphines. [62] During these comparative studies a range of DAN-phosphines and related compounds were synthesized by Schiemenz (Scheme 38) [62,63,[67][68][69] and (Scheme 34).…”