Intramolecular hypervalent CO?S interactions in a series of 1,3-benzothiazole derivatives?

CrystEngComm Pub Date: 2011-11-24 DOI: 10.1039/C1CE06106B

Abstract

Seven compounds derived from 2-(4-chlorophenoxy)-2-methylpropionic acid and 2-aminobenzothiazole, 2-amino-6-methylbenzothiazole, 2-amino-6-methoxybenzothiazole, 2-amino-6-ethoxybenzothiazole, 2-amino-6-chlorobenzothiazole, 2-amino-6-nitrobenzothiazole, and 2-amino-6-(methylsulfonyl) benzothiazole have been prepared and structurally characterized. This set of 1,3-benzothiazole derivatives (1–7) has been studied by means of elemental analysis, mass spectrometry, IR, NMR (1H, 13C) spectroscopy, and single-crystal X-ray diffraction analysis. This work focuses on the description of the hypervalent contacts (C[double bond, length as m-dash]O?S, S?S), hydrogen bonds Y–H?X (Y = O, N, C; X = O, N, Cl, π) and van der Waals contacts (Cl?π, S?π, H?H) that are found to be the driving forces for the supramolecular arrangements present in the crystal structures.

Graphical abstract: Intramolecular hypervalent C [[double bond, length as m-dash]] O?S interactions in a series of 1,3-benzothiazole derivatives
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