Pivalic Acid N-[Chloro(dimethyl)silylmethyl]-N-methylamide: Synthesis and Structure

• Published in: Russian journal of general chemistry Vol. 92; no. 8; pp. 1449 - 1456
• Main Authors: Lazareva, N. F., Sterkhova, I. V.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-08-2022; Springer; Springer Nature B.V
• Subjects: Bond energy; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Chlorine; Diffraction; Hydrogen atoms; NMR spectroscopy; Nuclear magnetic resonance spectroscopy; X-rays; pivalic acid; methylamide; dative bond; chloro(dimethylsilyl)methyl; (O–Si) chelate; NMR spectroscopy; X-ray diffraction analysis
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363222080126

Pivalic acid
N
-[chloro(dimethylsilyl)methyl]-
N
-methylamide was synthesized by the reaction of pivalic acid
N
-methylamide with (chloromethyl)dimethylchlorosilane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Using the methods of multinuclear NMR spectroscopy and X-ray diffraction analysis, it was proved that the compound exists in the form of an (O–Si) chelate with an intramolecular dative bond C=O→Si, the length of which is 1.943(1) Å. The dative bond energy, according to the QTAIM analysis, is 17.6 kcal/mol. In the crystal, the molecules of the obtained amide form an endless zigzag chain due to the existence of weak non-covalent interactions (2.884 Å) between the chlorine atoms and the hydrogen atoms of the NMe group of the neighboring molecule.