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The synthesis and stereoelectronic structure of 1- and 2-(trimethoxysilylmethyl)- and 1- and 2-(silatranylmethyl)benzotriazole

“…It is noteworthy that the N···Si interatomic distance in molecule 6 is almost coincident with the corresponding value in the molecule of (1-silatranylmethyl)-1,2,4-triazole (2.095 Å), 31 -pyrrole (2.089 Å), 32 -indole (2.11 Å) 33 and -carbazole (2.097 Å). 34 This testifies to the fact that the electron-accepting inductive effect is practically equal for all the above heterocyclic substituents. The displacement of the silicon atom from the bipyramidal equatorial plane towards the C 7 carbon atom is 0.14 Å.…”

“…30 In the heterocyclic fragment 6 the length of the exocyclic N 2 -C 7 bond (1.460 Å) is close to the standard length of a single bond (1.47 Å). Nearly the same length for the N-C 7 bond is observed in the molecules of (1-silatranylmethyl)-1,2,4-triazole (1.464 Å), 31 pyrrole (1.470 Å), 32 -indole (1.470 and 1.490 Å, for α-and β-, respectively) 33 and -carbazole (1.467 Å) . 34 The lengths of the endocyclic bonds С 9 -N 3 (1.360 Å) and C 8 -N 1 (1.364 Å) are similar, whereas those of the N 1 -N 2 (1.317Å) and N 2 -N 3 bonds (1.337 Å) are 0.02 Å different.…”

“…The SiC 7 N 2 angle of 117.8° in the molecule 6 is also analogous to that in the molecule of (1-silatranylmethyl)-1,2,4-triazole (117.9°), -pyrrole (116.9°), -indole (118.5 and 117.6°, for α-and β-, respectively) and -carbazole (117.5°). The bond lengths and valence angles in the silatranylmethyl fragment (Table 5) are close to those in (1-silatranylmethyl)-1,2,4-triazole, 31 pyrrole, 32 -indole, 33 and -carbazole. 34 The coordination polyhedron of the silicon atom in the molecule 6 shows a trigonal-bipyramidal configuration, typical of silatranes, with the N 4 nitrogen and С 7 carbon atoms in the axial positions.…”

“…The bond lengths and valence angles in the silatranylmethyl fragment (Table 5) are close to those in (1-silatranylmethyl)-1,2,4-triazole, 31 pyrrole, 32 -indole, 33 and -carbazole. 34 The coordination polyhedron of the silicon atom in the molecule 6 shows a trigonal-bipyramidal configuration, typical of silatranes, with the N 4 nitrogen and С 7 carbon atoms in the axial positions. The equatorial apexes of this polyhedron are occupied with О 1 , О 2 , О 3 oxygen atoms (Fig.…”

Silatranes: a review on their synthesis, structure, reactivity and applications

“…36 The resulting silatranes were further reacted with MeI to give new silatranes. 37 This method was found to be very efficient for the synthesis of 1-(N-silatranylmethyl)-1,2,4-triazole (41). 38 In continuation, condensation of [3-(triethoxysilyl)propyl]amine with 2-aminopyridine was carried out to synthesize 2-{ [3-(triethoxysilyl)propyl]amino}pyridine, which undergoes transesterification reaction to form 2-[(3-silatranylpropyl)amino]pyridine (42).…”