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Updated: May 21, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
O-Propyl N-phenyl-thio-carbamate
Abstract:
Two independent mol-ecules comprise the asymmetric unit in the title thio-carbamide derivative, C(10)H(13)NOS. These differ in the relative orientations of terminal ethyl groups [C-C-C-O torsion angles = -66.95 (13) and 55.92 (13)°, respectively]. The phenyl ring is twisted out of the plane of the central residue [C(q)-N-C(ph)-C(ph) = -146.20 (12) and -144.15 (12)°, respectively; q = quaternary and ph = phen-yl]. The independent mol-ecules are linked into a dimeric aggregate by N-H⋯S hydrogen bonds and an eight-membered thio-amide {⋯H-N-C=S}(2) synthon.
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The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Preparation of Nitriles