540 Chemie und zugeordnete Wissenschaften
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In the course of systematic investigations on sila-substituted parasympatholytics the diphenyl(2-aminoethoxymethyl)silanols 3b and 4b (and its carbon analogue 4a) were synthesized and characterized by their physical and chemical properties. In the solid state 4a and 4b form strong O-H---N hydrogen bonds, which are intramolecular (4a) and intermolecular (4b), respectively. 4a and 4b were found to be weak antimuscarinic agents (4b >4a) and strong papaverine-like spasmolytics (4a ≈4b).
The crystal structure of C12H11N2SiCl3 (monoclinic, P21/m, Z = 2, with a: 9.284(4), b: 7.226(2), c: 10.832(5) Å, β = 115.14(3)°) was refined to R(F) =0.035 from 1228 independent reflections. A trigonal bipyramidal, pentacoordinate silicon is observed. The chelated complex shows two different Si−N bonds, a coordinative bond (1.984(2) Å) between Si and N on the axial position and a Si−N single bond (1.737(3) A, equatorial plane), introduced by chemical reaction. The coordinative bond is 14.2% longer than the Si−N single bond. The lengthening of the coordinative bond in the present case is compared with distances in other extracoordinated silicon compounds.